[ CAS No. 52-89-1 ] {[proInfo.proName]}

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Quality Control of [ 52-89-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52-89-1 ]

SDS Specification

Alternatived Products of [ 52-89-1 ]

Product Details of [ 52-89-1 ]

CAS No. :	52-89-1	MDL No. :	MFCD00064553
Formula :	C₃H₈ClNO₂S	Boiling Point :	-
Linear Structure Formula :	SHCH₂CH(NH₂)COOH·HCl	InChI Key :	IFQSXNOEEPCSLW-DKWTVANSSA-N
M.W :	157.62	Pubchem ID :	60960
Synonyms :		Chemical Name :	(R)-2-Amino-3-mercaptopropanoic acid hydrochloride

Calculated chemistry of [ 52-89-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	35.91
TPSA :	102.12 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-1.69
Log Po/w (WLOGP) :	0.13
Log Po/w (MLOGP) :	-2.61
Log Po/w (SILICOS-IT) :	-0.69
Consensus Log Po/w :	-0.97

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.38
Solubility :	378.0 mg/ml ; 2.4 mol/l
Class :	Highly soluble
Log S (Ali) :	0.06
Solubility :	180.0 mg/ml ; 1.14 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.59
Solubility :	612.0 mg/ml ; 3.88 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 52-89-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 52-89-1 ]

* 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.

Upstream synthesis route of [ 52-89-1 ]
Downstream synthetic route of [ 52-89-1 ]

[ 52-89-1 ] Synthesis Path-Upstream 1~1

1
[ 52-89-1 ]
[ 1885-14-9 ]
[ 19771-63-2 ]

Reference： [1] Chemistry - A European Journal, 2004, vol. 10, # 23, p. 6102 - 6110
[2] Patent: EP1462444, 2004, A1, . Location in patent: Page 23
[3] European Journal of Pharmaceutics and Biopharmaceutics, 2016, vol. 103, p. 62 - 70

[ 52-89-1 ] Synthesis Path-Downstream 1~10

1
[ 76-84-6 ]
[ 52-89-1 ]
[ 2799-07-7 ]

Yield	Reaction Conditions	Operation in experiment
98%		Triphenylmethanol (3.3 g, 12.7 mmol) was added to a solution of Cysteine chlorydrate (2 g, 12.7 mmol) in TFA (25 mL) and the mixture was stirred for 2 h. After cooling to 0 °C, NaOH 4N and diethyl ether (40 mL) were added until pH 4-5 and then 10percent sodium acetate aqueous solution was added until pH 5-6. The precipitated obtained was filtered, washed with fresh Et2O and finally dried to obtain the desired product (5 g, 98percent yield).1H NMR (DMSO): delta (ppm) 2.35-2.61 (m, 2H, CH2); 2.85-2.98 (m, 1H, CH); 7.2-7.45 (m, 15H, trityl-H).MALDI-TOF MS: m/z364.7 Da [M + H]+, C22H21NO2S, Mol. Wt.: 363.47.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 383 - 392
[2]Chemical Communications,2013,vol. 49,p. 10808 - 10810
[3]Journal of the Chemical Society C: Organic,1970,p. 2687
[4]Journal of Medicinal Chemistry,1970,vol. 13,p. 414 - 418
[5]Canadian Journal of Chemistry,1981,vol. 59,p. 406 - 421

2
[ 52-89-1 ]
[ 76-83-5 ]
[ 2799-07-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	In N,N-dimethyl-formamide; at 20℃; for 48h;	L-Cysteine hydrochloride (100 g, 0.634 mol) and trityl chloride (270 g, 0.969 mol) were stirred in DMF (400 mL) for 2 days at room temperature. A 10percent sodium acetate solution (3.5 L) was then added dropwise and the white precipitate which formed was filtered and washed with distilled water. Afterward, the residue was stirred in acetone at 50° C. for 30 min after which it was cooled to 0° C. and filtered. The precipitate was washed with a little acetone and diethyl ether and dried in vacuo. S-Trityl-L-cysteine 1b (205 g, 89percent) was obtained as a white powder. 1b: m.p. 192° C. (decomp). 1H NMR (DMSO-d6) delta 2.45 (dd, 1H, J=9 Hz, 12 Hz), 2.58 (dd, 1H, J=4.4 Hz, 12 Hz), 2.91 (m, 1H), 7.22-7.36 (m, 15H); 13C NMR (75.5 MHz, DMSO-d6): delta 33.8, 53.7, 66.4, 127.1, 127.8, 128.1, 128.4, 129.5, 144.5, 168.4. This material was directly used in the next step without further purification.
89%	With sodium acetate; In N,N-dimethyl-formamide; at 20℃; for 48h;	L-Cysteine hydro-chloride (100 g, 0.634 mol) and trityl chloride (270 g, 0.969 mol) were stirred in DMF (400 mL) for 2 days at room temperature. A 10percent sodium acetate solution (3.5 L) was then added dropwise and the white precipitate which formed was filtered and washed with distilled water. Afterward, the residue was stirred in acetone at 50 0C for 30 min after which it was cooled to 00C and filtered. The precipitate was washed with a little acetone and diethyl ether and dried in vacuo. S-Trityl-L-cysteine Ic (205 g, 89percent) was obtained as a white powder. Ic: m.p. 192 °C (decomp) ; 1H NMR (300 MHz, DMSCW5) delta 2.45 (dd, IH, J= 9 Hz, 12 Hz), 2.58 (dd, IH, J= 4.4 Hz, 12 Hz), 2.91 (m, IH), 7.22-7.36 (m, 15H); 13C NMR (75.5 MHz, DMSO- d6): delta 33.8, 53.7, 66.4, 127.1, 127.8, 128.1, 128.4, 129.5, 144.5, 168.4. This material was directly used in the next step without further purification.
78%	In N,N-dimethyl-formamide; at 20℃; for 48h;	Preparation 75: Synthesis of (R)-3-amino-4-tritylsulfanyl-butyric acid methyl ester hydrochloride; (Step 1); L-cysteine hydrochloride (5Og, 284.7mmol) was dissolved in N,N- dimethylformamide (200ml). Trityl chloride (119g, 427.0mmol) was added thereto, and the mixture was stirred for 48 h at room temperature. After completion of the reaction, 10percent sodium acetate (1.5L) was added. The mixture was filtered to give a solid, which was then added to acetone (1.5L), and stirred for 30 min at 50 °C . The insoluble solid was filtered, and dried to give a trityl compound (80g, Yield 78percent).

77%

In N,N-dimethyl-formamide; at 20℃; for 48h;

Synthetic Example 1; (R)-3-Mercapto-2-(5-methyl-4-phenyl-thiazoI-2-yIamino)-propionic acid; Step 1 : S-Trityl-L-cysteine falso known as (R)-2-amino-3- (tritylsulfanyl)propanoic acid); L-Cysteine hydrochloride (5.0 g, 31.7 mmol) and trityl chloride (13.5 g, 48.4 mmol) were stirred in DMF (20 ml) for 48 h at room temperature. A 10percent NaOAc solution (175 mL) was then added, and the precipitate was filtered and washed with water. Afterward, the residue was suspended in acetone and stirred at 50 °C for 30 min, then cooled and filtered. The residue was washed with acetone (cold) and diethyl ether. After drying 8.86 g (77percent) S-trityl-L-cysteine was obtained.

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 619 - 626
[2]Patent: US7829709,2010,B1 .Location in patent: Page/Page column 19-20
[3]Patent: WO2009/100431,2009,A1 .Location in patent: Page/Page column 28
[4]Patent: WO2009/82152,2009,A2 .Location in patent: Page/Page column 214
[5]Patent: WO2009/151744,2009,A1 .Location in patent: Page/Page column 93
[6]Chemical Communications,2009,p. 407 - 409
[7]Acta Chemica Scandinavica (1947),1959,vol. 13,p. 383
[8]Journal of the American Chemical Society,1962,vol. 84,p. 3887 - 3897

3
[ 52-89-1 ]
[ 76-83-5 ]
[ 2799-07-7 ]
[ 27686-50-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1956,p. 698

4
[ 52-89-1 ]
[ 50606-58-1 ]
(5R)-7-benzyl-(5rC⁶)-1-thia-4,7-diaza-spiro[4.5]decane-3c-carboxylic acid [ No CAS ]

Reference： [1]Polish Journal of Chemistry,1978,vol. 52,p. 385 - 388

5
[ 52-89-1 ]
[ 939-69-5 ]
[ 37657-66-2 ]

Reference： [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074

6
[ 52-89-1 ]
[ 939-69-5 ]
[ 20240-21-5 ]

Reference： [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074

7
[ 497-09-6 ]
[ 52-89-1 ]
[ 124617-03-4 ]

Reference： [1]Carbohydrate Research,1989,vol. 187,p. 223 - 238

8
[ 27829-72-7 ]
[ 52-89-1 ]
2-amino-3-[(2-ethoxycarbonyl-1-propylethyl)sulfanyl]propionic acid [ No CAS ]

Reference： [1]Chimia,2007,vol. 61,p. 533 - 535

9
[ 7724-12-1 ]
[ 52-89-1 ]
potassium (S)-2-(6-aminobenzo[d]thiazol-2-yl) -4,5-dihydrothiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		D-Cysteine hydrochloride monohydrate (81.2 mg, 0.462 mmol, 1.1 eq) and 6-amino-cyano- benzothiazole (71 .0 mg, 0.405 mmol, 1 eq) were dissolved in 2:1 MeOH:H20 (1 mL). The resulting solution was allowed to stir at room temperature for 5 mm under a nitrogen atmosphere, after which potassium carbonate (56.5 mg, 0.409 mmol, 1.01 eq) was added. The resulting brightyellow-green solution was allowed to stir for an additional 40 mm, while maintaining an inert atmosphere. Upon consumption of 6-amino-cyanobenzothiazole, as evidenced by TLC analysis, the reaction mixture was diluted with water (4 mL) and washed with EtOAc (1 x 4 mL). The aqueous was then reduced and the resulting precipitate was filtered and washed with cold MeOH (2 x 1 mL). The precipitate was then further purified using reverse phase chromatography elutingwith a gradient of 0-90percent MeOH in water to afford D-aminoluciferin postassium salt as a paleyellow solid (0.123 g, 96percent). [c]ObS: -14° (H20, c = 1). Mp: 111-123°C. 1H-NMR (400 MHz, D20)68.32 (1H, d, J= 8.8 Hz, H-7), 7.79 (1H, s, H-b), 7.55 (1 H, d, J= 8.0 Hz, H-8), 5.72 (1H, m, H-2), 3.8-4.2 (2H, m, H-3). HRMS (ESI+): m/zCalculated for C11H9N302S2K [M+H] 317.9773, found317.9768.

Reference： [1]Patent: WO2019/21202,2019,A1 .Location in patent: Page/Page column 28

10
[ 52-89-1 ]
[ 939-69-5 ]
[ 2591-17-5 ]

Yield	Reaction Conditions	Operation in experiment
86%		D-Cysteine hydrochloride monohydrate (30.0 mg, 0.171 mmcl, 1.04 eq) and 2-cyano-6-hydroxy- benzothiazole (29.0 mg, 0.163 mmol, 1 eq) were dissolved in 2:1 MeOH:H20 (1 mL). The resultingsolution was allowed to stir at room temperature for 5 mm under a nitrogen atmosphere, after which potassium carbonate (23.0 mg, 0.164 mmol 1.01 eq) was added. The resulting bright yellow-green solution was allowed to stir for an additional 20 mm, at room temperature, while maintaining the inert atmosphere. Upon consumption of <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, as evidenced by TLC analysis, the methanol was removed in vacuo and the remaining aqueoussolution cooled to 0 °C and acidified to pH 3 with 3 M HCI. The aqueous layer was then extracted with EtOAc (5 x 10 mL) and the combined organ ics were dried over Na2SO4, filtered, concentrated in vacuo and purified with column chromatography 3:6:1 DCM:EtOAc:MeOH to provide D-luciferin as a pale yellow solid (39.0 mg, 86 percent). [c]ObS = 290, DMF, c = 1 ([a]1. = -34°, DMF, c = 1). Mp:197-199°C (lit. 196 °C).3 1H-NMR (400 MHz, MeOD) (57.93 (1H, d, J= 8.9 Hz, H-7), 7.35 (iH, d,J= 2.3 Hz, H-b), 7.10 (1H, dd, J= 8.9, 2.3 Hz, H-8), 5.40 (iH, appt, J= 9.0 Hz, H-2), 3.79 (2H, m, H-3) ppm. 13C-NMR (100.6 MHz, CDCI3) oe 172.1 (C-i), 166.2 (C-4), 157.6 (C-9), 157.1 (C-5), 146.8 (C-6), 137.7 (C-il), 124.5 (C-7), 116.8 (C-b), 105.9 (C-8), 78.2 (C-2), 34.5 (C-3) ppm. HAMS (ESI+): m/zCalculated for C11H8N20352 [M+Na] 302.9874, found 302.9868.
80%	With potassium carbonate; In methanol; dichloromethane; water; for 0.166667h;Cooling with ice;	<strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong> (100 mg, 0.57 mmol) was dissolved in DCM:MeOH = 2:3 (10 mL: 15 mL).And pass N2 to the solution.D-cysteine hydrochloride (136 mg, 0.86 mmol) and K2CO3 (119 mg, 0.86 mmol) were dissolved in DI H2O:MeOH = 1:1 (3 mL).The solution was added dropwise to the above <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, and the reaction was carried out in the ice bath for 10 min.After the reaction was completed, DCM and MeOH were distilled off under reduced pressure.The pH was then adjusted to 2-3 with a solution of hydrochloric acid (1M) and a yellow precipitate precipitated.The precipitate was filtered and washed with DI H 2 O until the pH became neutral to give D-luciferin crude product.By column chromatography (silica, DCM: MeOH: AcOH, 10:1:1 v/v/v)Purification gave 128 mg of a pale yellow solid.The yield was 80percent.

Reference： [1]Patent: WO2019/21202,2019,A1 .Location in patent: Page/Page column 28
[2]Patent: CN109293653,2019,A .Location in patent: Paragraph 0109-0110

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Isomers

Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 52-89-1 ] {[proInfo.proName]}

Quality Control of [ 52-89-1 ]

Related Doc. of [ 52-89-1 ]

Product Details of [ 52-89-1 ]

Calculated chemistry of [ 52-89-1 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 52-89-1 ]

Application In Synthesis of [ 52-89-1 ]

[ 52-89-1 ] Synthesis Path-Upstream 1~1

[ 52-89-1 ] Synthesis Path-Downstream 1~10

Technical Information

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