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[ CAS No. 6964-21-2 ] {[proInfo.proName]}

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Chemical Structure| 6964-21-2
Chemical Structure| 6964-21-2
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Quality Control of [ 6964-21-2 ]

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Product Details of [ 6964-21-2 ]

CAS No. :6964-21-2 MDL No. :MFCD00005473
Formula : C6H6O2S Boiling Point : No data available
Linear Structure Formula :SC4H3CH2CO2H InChI Key :RCNOGGGBSSVMAS-UHFFFAOYSA-N
M.W : 142.18 Pubchem ID :23404
Synonyms :

Calculated chemistry of [ 6964-21-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.86
TPSA : 65.54 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 0.72
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.63
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.45
Solubility : 5.0 mg/ml ; 0.0351 mol/l
Class : Very soluble
Log S (Ali) : -1.67
Solubility : 3.01 mg/ml ; 0.0212 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.42
Solubility : 5.42 mg/ml ; 0.0381 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 6964-21-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6964-21-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6964-21-2 ]

[ 6964-21-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 67-56-1 ]
  • [ 6964-21-2 ]
  • [ 58414-52-1 ]
YieldReaction ConditionsOperation in experiment
100% With acetyl chloride; at 0 - 20℃; Acetyl chloride (7.50 ml, 106 mmol) was added dropwise to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (5.00 g, 35.3 mmol) in dry MeOH (150 ml) at 0 C. The mixture was left to slowly reach room temperature and stirred overnight. Solvents were evaporated and residue filtered through a short plug of silica gel (DCM) to give a quantitative yield of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.64 (s, 2H), 3.70 (s, 3H), 7.03-7.05 (m, 1H), 7.14-7.15 (m, 1H), 7.27-7.29 (m, 1H).
100% With acetyl chloride; at 0 - 20℃; Acteyl chloride (7.50 ml, 106 mmol) was added dropwise to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (5.00 g, 35.3 mmol) in dry MeOH (150 ml) at 0 C. The mixture was left to slowly reach room temperature and stirred overnight. Solvents were evaporated and residue filtered through a short plug of silica gel (DCM) to give a quantitative yield of the title compound an oil. 1H MR (400 MHz, CDC13): 3.64 (s, 2H), 3.70 (s, 3H), 7.03-7.05 (m, 1H), 7.14 7.15 (m, 1H), 7.27-7.29 (m, 1H).
80% With sulfuric acid; at 0℃; for 14h;Reflux; To a stirred solution of 2-(thiophen3-yflacetic acid (5 g, 35.2 mmoi) in methanol (60 ml) at 0 cc was added drop wise solution of H2S04 (6.92 ml, 130 mmofl, The reaction mixture was refluxed for 1 4h, After completion of reaction, methanol was evaporated and residue was further diluted with dichioromethane, An organic layer was washed with saturated sodium bicarbonate solution and evaporated under reduced pressure to afford methyl 2-(thiophen-3-yl)acetate (4.4 g, 80%) as oil.
With sulfuric acid; for 24h;Reflux; [00165] Methyl thiophene-3-acetate LXXXIV (M3) was synthesized following the method reported by Kim, L. Chen, Gong, Y. Osada, Macromolecules 1999, 32, 3964- 3969, the disclosure of which is incorporated herein by reference in its entirety. Briefly, 3-Thiopheneacetic acid (8.52 g, 60 mmol) was dissolved in 50 mL of methanol with 2 drops of concentrated H2504. The mixture was heated in an oil bath and refluxed for 24 hours. After the removal of methanol, the crude product was redissolved in diethylether, washed with DI water and dried with anhydrous magnesium sulfate. Pure product was obtained after filtration and evaporation of solvent. The structure was analyzed and confirmed with ‘H NMR spectroscopy.
With thionyl chloride; at 0 - 68℃; for 12h; To a solution of 2-(3-thienyl)acetic acid (12.1, 5.40 g, 37.9 mmol, 1 equivalent) in MeOH (50 mL) was added thionyl chloride (6.78 g, 56.9 mmol, 4.13 mL, 1.5 equivalent) at 0 C. The mixture was heated to 68 C. for 12 hours. After this time, the reaction solution was evaporated and to this residue was added saturated sodium bicarbonate solution (80 mL). The suspension was extracted with ethyl acetate (35 mL*3), then dried over sodium sulfate and the solvent was removed to afford methyl 2-(thiophen-3-yl)acetate (12.2, 5.8 g, yield=93%) as a yellow oil without further purification.
With thionyl chloride; at 0 - 25℃; for 1h; To a solution of 2-(thiophen-3-yl)acetic (500 mg, 3.52 mmol) in MeOH (5 ml) at 0 C was added SOCl2 (1.02 ml, 14.07 mmol) and stirred at 25 C for 1 h. The RM was concentrated in vacuo to give methyl 2-(thiophen-3-yl)acetate as a yellow oil.1H NMR (400 MHz, MeOD) d 7.35 (dd, J = 5, 3 Hz, 1H), 7.21 (dd, J = 3, 1 Hz, 1H), 7.03 (dd, J = 5, 1 Hz, 1H), 3.69 (s, 3H), 3.63 (s, 2H).

  • 2
  • [ 6964-21-2 ]
  • [ 13781-65-2 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride;N,N-dimethyl-formamide; In tetrahydrofuran; The procedure described above for the synthesis of 1-chloro-3-[2-(3-methylbenzo[b]thiophen-2-yl)propan-2-one was followed, reacting thiophene-3-acetic acid (5.32 g, 37.4 mmol) with oxalyl chloride (3.6 mL, 5.2 g, 41 mmol, then ethereal diazomethane, then dry HCl gas. Work-up gave pure product, a brown oil which solidified upon refrigeration to a golden-brown, waxy solid (6.52 g, 100% yield): 1H NMR (400 MHz, CDCl3) δ 3.94 (s, 2H) 4.13 (s, 2H) 6.99 (d, J=5.1 Hz, 1H) 7.16 (dd, J=1.5, 0.8 Hz, 1H) 7.33 (dd, J=4.9, 2.9 Hz, 1H).
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h; General method 2: preparation of ethyl-5-substituted-1 ,2,4-oxadiazole-3carboxylateStep I A mixture of a 2-aryl acetic acid (3.78 mmol; 1 equivalent) and oxalyl chloride (4.16 mmol,1.1 equivalents) in dichloromethane (12 ml_) with few drops of DMF was stirred at room temperature for 3 h.Step IlThe resulting solution from step I was added to a mixture of ethyl 2-amino-2- (hydroxyimino)acetate (3.78 mmol 1 equivalent) and N1N diisopropylethylamine (6.06 mmol, 1.60 equivalents) in dichloromethane (6 ml.) at -15C. The reaction mixture was then stirred at room temperature for 12 to 36 h and poured into a mixture of ice and water. The formed precipitate was filtered off. When a precipitate was not formed, the organic layer was separated, dried over magnesium sulphate, filtered and evaporated to dryness. Step III The precipitate or the residue from step Il was refluxed in a sealed tube with pyridine (18 ml.) for 20 h and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica to yield the desired compound.; INTERMEDIATE 105 - PREPARATION OF ethyl 5-(thiophen-3-ylmethyl)-1 ,2,4- oxadiazole-3-carboxylate; This compound was prepared according to general method 2 with (step I) 2-(thiophen-3- yl)acetic acid (0.568 g; 3.78 mmol), oxalyl chloride (0.352 ml 4.16 mmol) in dichloromethane (12 ml.) with few drops of DMF; (step II) ethyl 2-amino-2- (hydroxyimino)acetate (0.5 g; 3.78 mmol); N, N diisopropylethylamine (1.05 ml 6.06 mmol) in dichloromethane (6 mL) and (step III) pyridine (18 ml_).The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.343 g (38%) of ethyl 5-(thiophen-3-ylmethyl)-1 ,2,4-oxadiazole-3-carboxylate as a yellow solid. ESI/APCI(+): 239(M+H).
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 18h;Inert atmosphere; General procedure: Carboxylic acid (0.735 mmol, 1.0 eq.) was added to a flame dried microwave vial under Argon. DCM (3 mL) was added, followed by oxalyl chloride (0.075mL, 0.885 mmol, 1.2 eq) and DMF (1 drop). The reaction mixture was stirred at room temperature under Argon for 18 hours. The solvent was removed under reduced pressure to afford the crude product. The resulting crude material was used directly for the next step without further purification.
  • 3
  • [ 6964-21-2 ]
  • [ 77014-10-9 ]
  • 4
  • [ 6964-21-2 ]
  • [ 79-22-1 ]
  • [ 58414-52-1 ]
  • 5
  • [ 6964-21-2 ]
  • [ 64-17-5 ]
  • [ 37784-63-7 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid; for 24h;Reflux; Step 1: Preparation of ethyl 2-(thiophen-3-yl)acetate 10.75 g (74.1 mmol) of 2-(thiophen-3-yl)acetic acid were solubilized in 100 ml of ethanol, 6 ml (72 mmol) of sulfuric acid were added to this solution. The mixture was heated with magnetic stirring with reflux for 24 h. After returning to r.t., the mixture was concentrated in vacuo, the crude residue was treated with 100 ml of a mixture consisting of water and ice. The aqueous phase was extracted with 2*100 ml of ethyl acetate. The combined organic phases were washed with 100 ml of water, 100 ml of a saturated NaHCO3 aqueous solution and 100 ml of a saturated NaCl aqueous solution and then dried on MgSO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo in order to obtain 12.27 g (yield=97%) of ethyl 2-(thiophen-3-yl)acetate as a colorless oil. LC-MS: m/z=non-ionized. 1H NMR (300 MHz, CDCl3) δ 7.24 (dd, J=6.0, 3.0 Hz, 1H), 7.16-7.07 (m, 1H), 7.02 (dd, J=4.9, 1.1 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.62 (s, 2H), 1.23 (t, J=7.1 Hz, 3H).
97% With sulfuric acid; for 24h;Reflux; 10.75 g (74.1 mmol) of 2-(thiophen-3-yl)acetic acid were solubilized in 100 ml of ethanol, 6 ml (72 mmol) of sulfuric acid were added to this solution. The mixture was heated with magnetic stirring with reflux for 24 h. After returning to r.t., the mixture was concentrated in vacuo, the crude residue was treated with 100 ml of a mixture consisting of water and ice. The aqueous phase was extracted with 2*100 ml of ethyl acetate. The combined organic phases were washed with 100 ml of water, 100 ml of a saturated NaHCO3 aqueous solution and 100 ml of a saturated NaCl aqueous solution and then dried on MgSO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo in order to obtain 12.27 g (yield=97%) of ethyl 2-(thiophen-3-yl)acetate as a colorless oil. LC-MS: m/z=non-ionized. 1H NMR (300 MHz, CDCl3) δ 7.24 (dd, J=6.0, 3.0 Hz, 1H), 7.16-7.07 (m, 1H), 7.02 (dd, J=4.9, 1.1 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 3.62 (s, 2H), 1.23 (t, J=7.1 Hz, 3H).
  • 6
  • [ 6964-21-2 ]
  • 1,3-di(thiophen-3-yl)propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Take a 100mL round bottom flask,DCC (1.0320g, 5mmol)And DMAP (0.1222 g, 1 mmol) was added to 10 mL of dry dichloromethane.Stir until all dissolved.3-Thiopheneacetic acid (0.7109 g, 5 mmol) was dissolved in 20 mL of dry dichloromethane, and then slowly added dropwise to the above solution using a constant pressure dropping funnel.Stir for 24-72h.It was dried to dryness and then subjected to column chromatography (eluent: ethyl acetate: petroleum ether: = 1:5) to give the title compound.
  • 7
  • [ 6964-21-2 ]
  • [ 58414-52-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 This Example illustrates the preparation of (E)-methyl 3-methoxy-2-(3-thienyl)propenoate (compound number 1 of Table II). Methyl 3-thienylacetate was prepared by heating 3-thienylacetic acid in acidic methanol. It is an oil, 1H nmr: delta 3.71 (2H,s), 3.76 (3H,s) ppm.
  • 8
  • [ 6964-21-2 ]
  • [ 34967-61-8 ]
YieldReaction ConditionsOperation in experiment
72% With N-chloro-succinimide; In acetic acid; at 20℃; for 12h; A solution of 3-thiophene acetic acid (1.42 g, 10.0 mmol) in acetic acid (10 mL) was treated with N-chlorosuccinimide (3. 1 g, 23 mmol, 2.3 equivalents), and the solution was stirred for 12 h at room temperature then concentrated in vacuo. The residue was diluted with water and stirred for 1 h whereupon the resulting solid was collected by filtration. The solid was dried in a vacuum oven at room temperature for 10 hours providing 1.51 g (72%) of (2, 5-dichlorothien-3-vl) acetic acid as a brown solid, which was used as such in the next step. MS (ESI) m/z 209/211/213 ( [M-H]-).
72% With N-chloro-succinimide; In acetic acid; at 20℃; for 12h; A solution of 3-thiophene acetic acid (1.42 g, 10.0 mmol} in acetic acid (10 mL) was treated with N-chlorosuccinimide (3. 1g, 23 mmol, 2.3 equivalents), and the solution was stirred for 12 h at room temperature then concentrated in vacuo. The residue was diluted with water and stirred for 1 h whereupon the resulting solid was collected by filtration. The solid was dried in a vacuum oven at room temperature for 10 hours providing 1.51 g (72%) of (2. 5-dichlorothien-3-yl) acetic acid as a brown solid, which was used as such in the next step. MS (ESI) m/z 209/211/213 ( [M-H]-).
72% With N-chloro-succinimide; In acetic acid; at 20℃; for 12h; Step 1: A solution of 3-thiophene acetic acid (1.42 g, 10.0 mmol) in acetic acid (10 mL) was treated with N-chlorosuccinimide (3. 1g, 23 mmol, 2.3 equivalents), and the solution was stirred for 12 h at room temperature then concentrated in vacuo. The residue was diluted with water and stirred for 1 h whereupon the resulting solid was collected by filtration. The solid was dried in a vacuum oven at room temperature for 10 hours providing 1.51 g (72%) of (2, 5-dichlorothien-3-yl) acetic acid as a brown solid, which was used as such in the next step. MS (ESI) m/z 209/211/213 ( [M-H]-).
72% With N-chloro-succinimide; In acetic acid; at 20℃; for 12h; Example 141: 1-(2, 5-dichlorothien-3-vl)-2-piperazine-1-ylethyllcyclohexanol dihvdrochloride [0391] Step 1: A solution of 3-thiophene acetic acid (1.42 g, 10.0 mmol) in acetic acid (10 mL) was treated with N-chlorosuccinimide (3. 1g, 23 mmol, 2.3 equivalents), and the solution was stirred for 12 h at room temperature then concentrated in vacuo. The residue was diluted with water and stirred for 1 h whereupon the resulting solid was collected by filtration. The solid was dried in a vacuum oven at room temperature for 10 hours providing 1.51 g (72%) of (2. 5-dichlorothien-3-yl) acetic acid as a brown solid, which was used as such in the next step. MS (ESI) m/z 209/211/213 ( [M-H]-).
72% With N-chloro-succinimide; In acetic acid; at 20℃; for 12h; A solution of 3-thiophene acetic acid (1.42 g, 10.0 mmol) in acetic acid (10 mL) was treated with N-chlorosuccinimide (3. 1g, 23 mmol, 2.3 equivalents), and the solution was stirred for 12 h at room temperature then concentrated in vacuo. The residue was diluted with water and stirred for 1 h whereupon the resulting solid was collected by filtration. The solid was dried in a vacuum oven at room temperature for 10 hours providing 1.51 g (72%) of (2. 5-dichlorothien-3-yl) acetic acid as a brown solid, which was used as such in the next step. MS (ESI) m/z 209/211/213 ( [M-H]-).

  • 9
  • [ 6964-21-2 ]
  • [ 86966-03-2 ]
  • N-[(thien-3-yl)acetyl]alanine iso-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example B60 Synthesis of N-[(3-thienyl)acetyl]alanine Iso-butyl Ester Following General Procedure BI above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure BJ above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H).
Example B60 Synthesis of N-[(3-Thienyl)acetyl]alanine iso-Butyl Ester Following General Procedure BI above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure BJ above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure.
Example 60 Synthesis of N-[(3-thienyl)acetyl]alanine iso-butyl ester Following General Procedure I above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure J above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1 H-nmr (CDCl3): δ=7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H).
EXAMPLE A60 Synthesis of N-[(3-thienyl)acetyl]alanine iso-butyl ester Following General Procedure I' above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H).
EXAMPLE A60 Synthesis of N-[(3-thienyl)acetyl]alanine Iso-butyl Ester Following General Procedure I' above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H).
Example A60 Synthesis of N-[(3-thienyl)acetyl]alanine iso-butyl ester Following General Procedure I' above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H).
With 1-(3-(1-pyrrolidinyl)-propyl)-3-ethylcarbodiimide; In chloroform; at 23℃; for 96h; Example 60 Synthesis of N-[(3-thienyl)acetyl]alanine iso-butyl ester Following General Procedure I above, and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and alanine iso-butyl ester (prepared following General Procedure J above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ = 7.33 (m, 1H), 7.14 (m, 1H), 7.01 (m, 1H), 6.09 (m, 1H), 4.58 (m, 1H), 3.88 (m, 2H), 3.60 (s, 2H), 1.91 (m, 1H), 1.37 (d, 3H) 0.92 (d, 6H). Optical Rotation: [α]23-52 (c 1 MeOH) ? 589 nm. C13H19NO3S (MW = 269, Mass Spectroscopy (MH+ 269)). GENERAL PROCEDURE IP-EPC coupling P-EPC coupling employs an amino acid ester and a substituted acetic acid compound. The acetic acid derivative is well known in the art and is typically commercially available. The amino acid ester is prepared by conventional methods from the known and typically commercially available N-BOC amino acid as described in GENERAL PROCEDURE J below. Specifically, the appropriate amino ester free base (0.0346 mmols) and substituted phenylacetic acid (0.069 mmols) were dissolved in 2.0 mL CHCl3 (EtOH free), treated with 150 mg of P-EPC (0.87 meq./g) and the reaction was mixed for 4 days at 23C. The reaction was filtered through a plug of cotton, rinsed with 2.0 mL of CHCl3 and the filtrate evaporated under a stream of nitrogen. The purity of each sample was determined by 1H NMR and ranged from 50% to >95%. Between 8.0 and 15.0 mg of final product was obtained from each reaction and was tested without additional purification

  • 10
  • [ 6964-21-2 ]
  • iso-butyl 2-aminobutyrate [ No CAS ]
  • 2-[(thien-3-yl)acetamido]butyric acid iso-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example B18 Synthesis of 2-[(thien-3-yl)acetamido]butyric Acid Iso-butyl Ester Following General Procedure BI above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure BJ above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H).
Example B18 Synthesis of 2-[(Thien-3-yl)acetamido]butyric Acid iso-Butyl Ester Following General Procedure BI above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure BJ above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H).
Example 18 Synthesis of 2-[(thien-3-yl)acetamido]butyric acid iso-butyl ester Following General Procedure I above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure J above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1 H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1i), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H).
EXAMPLE A18 Synthesis of 2-[(thien-3-yl)acetamido]butyric acid iso-butyl ester Following General Procedure I' above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H).
Example A18 Synthesis of 2-[(thien-3-yl)acetamido]butyric Acid Iso-butyl Ester Following General Procedure I' above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tIc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, H), 0.91 (d, 61), 0.86 (t, 3H).
EXAMPLE A18 Synthesis of 2-[(thien-3-yl)acetamido]butyric Acid Iso-butyl Ester Following General Procedure I' above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure J' above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ=7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H).
With 1-(3-(1-pyrrolidinyl)-propyl)-3-ethylcarbodiimide; In chloroform; at 23℃; for 96h; Example 18 Synthesis of 2-[(thien-3-yl)acetamido]butyric acid iso-butyl ester Following General Procedure I above and using <strong>[6964-21-2]3-thiopheneacetic acid</strong> (Aldrich) and iso-butyl 2-aminobutyrate (prepared following General Procedure J above), the title compound was prepared. The reaction was monitored by tlc on silica gel and purification was by filtration as described in the general procedure. NMR data was as follows: 1H-nmr (CDCl3): δ = 7.37 (m, 1H), 7.16 (m, 1H), 7.04 (m, 1H), 6.05 (bd, 1H), 4.57 (m, 1H), 3.66 (s, 2H), 1.93 (m, 2H), 1.67 (m, 1H), 0.91 (d, 6H), 0.86 (t, 3H). GENERAL PROCEDURE IP-EPC coupling P-EPC coupling employs an amino acid ester and a substituted acetic acid compound. The acetic acid derivative is well known in the art and is typically commercially available. The amino acid ester is prepared by conventional methods from the known and typically commercially available N-BOC amino acid as described in GENERAL PROCEDURE J below.Specifically, the appropriate amino ester free base (0.0346 mmols) and substituted phenylacetic acid (0.069 mmols) were dissolved in 2.0 mL CHCl3 (EtOH free), treated with 150 mg of P-EPC (0.87 meq./g) and the reaction was mixed for 4 days at 23C. The reaction was filtered through a plug of cotton, rinsed with 2.0 mL of CHCl3 and the filtrate evaporated under a stream of nitrogen. The purity of each sample was determined by 1H NMR and ranged from 50% to >95%. Between 8.0 and 15.0 mg of final product was obtained from each reaction and was tested without additional purification

  • 11
  • [ 6964-21-2 ]
  • [ 863228-89-1 ]
  • C27H32N4O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; EXAMPLE 13; 3-[4-(5-Methoxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-phenyl]-2-[3-methyl-2-(2-thiophen-3-yl-acetylamino)-butyrylamino]-propionic acid, Cpd 107; A solution of Compound 12a (17 mg, 0.027 mmol), Compound 13a (4 mg, 0.03 mmol), EDC (8 mg, 0.04 mmol), HOBt (7 mg, 0.054 mmol), and DIEA (16 μL, 0.09 mmol) in 5 mL of CH2Cl2 was allowed to stir at rt overnight. The mixture was washed with 10% citric acid (aq) followed by saturated NaHCO3 (aq) solution. The organic layer was dried (MgSO4), filtered, and concentrated to yield Compound 13b (12 mg).
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