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CAS No. : | 6723-30-4 | MDL No. : | MFCD01321374 |
Formula : | C5H11NO2 | Boiling Point : | - |
Linear Structure Formula : | (CH2)4OCHONH2 | InChI Key : | NLXXVSKHVGDQAT-UHFFFAOYSA-N |
M.W : | 117.15 | Pubchem ID : | 5142091 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; at 20℃; for 2h; | NH2OTHP (0.38 g, 3.21 mmol) was added to a solution of trans-3-indoleacrylic acid (17) (0.50 g, 2.67 mmol), PyBOP (1.47 g, 2.83 mmol), triethylamine (0.74 ml, 6.41 mmol) in THF (25 mL). The mixture was stirred at room temperature for 2 h and then was concentrated under reduced pressure. The residue was dissolved in EtOAc and quenched with water, followed by extraction with EtOAc (20 mL*3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc:n-hexane=1.5:1:1% NH3(aq)) to afford 18. 1H NMR (500 MHz, CD3OD): delta 1.58-1.70 (m, 3H), 1.79-1.90 (m, 3H), 3.63-3.65 (m, 1H), 4.03-4.08 (m, 1H), 4.97-4.98 (m, 1H), 6.47 (d, J=14.9 Hz, 1H), 7.15-7.21 (m, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.59 (s, 1H), 7.84-7.87 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 31h; | The resulting <strong>[10601-99-7]3-ethynylbenzoic acid</strong> in step 3 (106) (669mg), was dissolved in EDCI (1.49 g), HOBt ·H2O (1.19 g), NH2OTHP (1.07 g) DMF (10 mL), It was stirred for 31 hours at room temperature. Water (100 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100mL). The organic layer saturated sodium bicarbonate (100 mL), washed with saturated brine (100 mL), dried over anhydroussodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, the residue was purified by silica gel flashcolumn chromatography (developing solvent nhexane:ethyl acetate = 1: 1) to give 3ethynylN(2tetrahydropyranyloxy)benzamide (107) the (1.04 g, 93% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 19h;Inert atmosphere; | Fmoc-L-propargylglycine (511 mg, 1.49 mmol) and THP-O-NH2 (219 mg, 1.64 mmol) were dissolved inanhydrous CH2Cl2 (2.5 mL) under Ar gas. In a separate flask, DCC (340 mg, 1.64 mmol) was dissolvedin anhydrous CH2Cl2 (3.5 mL) under Ar gas and transferred dropwise to the solution containingFmoc-L-propargylglycine and THP-O-NH2 at 0 C. The reaction mixture was then warmed to r.t. andran for 19 h. The crude mixture was filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (CH2Cl2:MeOH, 5percent) to afford 13 (642 mg, 96percent) as a whitesolid. Rf (CH2Cl2?MeOH, 5percent) = 0.66. 1H-NMR (CDCl3): delta 9.99 (br s, 1H), 7.73 (d, J = 7.4 Hz, 2H),7.56 (d, J = 7.0 Hz, 2H), 7.37 (t, J = 7.5 Hz, 2H), 7.27 (t, J = 7.5 Hz, 2H), 5.99 (d, J = 7.8 Hz, 1H), 5.27 (s, 2H),4.95 (br s, 1H), 4.54?4.26 (m, 3H), 4.18 (t, J = 7.0 Hz, 1H), 3.88 (t, J = 10.0 Hz, 1H), 3.52 (d, J = 11.1 Hz,1H), 2.69 (br s, 2H), 2.10?2.02 (m, 1H), 1.85?1.70 (m, 2H), 1.63?1.42 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; | To an oven dried round bottomed flask, charged with a magnetic stir bar were added EDC (0.76?g, 3.96?mmol), DIPEA (0.512?mL, 3.96?mmol), NH2OTHP (0.26?g, 2.18?mmol) <strong>[117-78-2]anthraquinone-2-carboxylic acid</strong> (0.5?g, 1.98?mmol) in DMF (50?mL) under argon atmosphere. The mixture was stirred at room temperature for 12?h. After completion, the reaction mixture was extracted with DCM. The organic layer was washed with 1N HCl followed by brine, dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatograpy to afford compound 2 in 21% yield. Rf?=?0.18 (3:7 ethyl acetate: hexane). 1H NMR (500?MHz, DMSO-d6) delta 8.56 (s, 1H), 8.30 (d, J?=?8.0?Hz, 1H), 8.26-8.22 (m, 3H), 7.97-7.94 (m, 2H), 5.07 (s, 1H), 4.09 (s, 1H), 3.57 (d, J?=?10.9?Hz, 1H) 1.75-1.57 (m, 6H). 13C NMR (125?MHz, DMSO-d6) delta 182.2, 182.1, 162.6, 137.2, 134.9, 134.7, 133.2, 133.1, 132.9, 127.2, 126.9, 126.9, 125.5, 101.1, 61.4, 27.8, 24.7, 18.2 ESI MS (m/z)?=?350.10 [M?-?H]+. |
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