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CAS No. : | 1413936-87-4 | MDL No. : | MFCD23773497 |
Formula : | C13H19NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 221.30 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
28% | Diphenylphosphoryl azide (508 mg, 1.85 mmol) was added to a tetrahydrofuran (8 mL) suspension of <strong>[36157-42-3]5-chlorothiophene-3-carboxylic acid</strong> () (250 mg, 1.54 mmol) and triethylamine (298 muL, 2.15 mmol), the resultant was stirred at room temperature for 7 minutes, and then, N,N-dimethylformamide (3 mL) was added thereto, followed by stirring at room temperature for 80 minutes. Benzyl 2-amino-2-ethylbutanoic acid (, ) (408 mg, 1.85 mmol) was added thereto, followed by stirring at 70C for 4.5 hours. The resultant was cooled to room temperature, saturated sodium bicarbonate was added thereto, and the resultant was extracted with ethyl acetate. The thus obtained extract was washed successively with water and a saturated saline solution, and dried over anhydrous sodium sulfate. A residue obtained through filtration and concentration under reduced pressure was purified by silica gel column chromatography [elution solvent: n-hexane/ethyl acetate = 9/1 - 3/1 (V/V)] to obtain 162 mg (28%) of the title compound in the form of a white solid. 1H-NMR (400MHz, CDCl3) delta: 7.36-7.30 (5H, m), 6.83 (1H, d, J = 2.0 Hz), 6.78 (1H, d, J = 2.0 Hz), 6.40 (1H, s), 5.64 (1H, s), 5.16 (2H, s), 2.46-2.37 (2H, m), 1.85-1.76 (2H, m), 0.70 (6H, t, J = 7.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: 5-Chlorothiophene-2-carboxylic acid With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 0.5h; Stage #2: benzyl 2-amino-2-ethylbutanoate In toluene at 80℃; for 3.5h; | 28.28a Benzyl 2-[(5-chlorothiophen-2-yl)carbamoyl]amino}-2-ethylbutanoic acid Diphenylphosphoryl azide (406 mg, 1.48 mmol) was added to a toluene (4.9 mL) solution of 5-chlorothiophene-2-carboxylic acid () (200 mg, 1.23 mmol) and triethylamine (239 μL, 1.72 mmol) at 0°C, the resultant was stirred at room temperature for 30 minutes, and then, benzyl 2-amino-2-ethylbutanoic acid () () (272 mg, 1.23 mmol) was added thereto, followed by stirring at 80°C for 3.5 hours. The resultant was cooled to room temperature, saturated sodium bicarbonate was added thereto, and the resultant was extracted with ethyl acetate. The thus obtained extract was washed with a saturated saline solution, and dried over anhydrous sodium sulfate. A residue obtained through filtration and concentration under reduced pressure was purified by silica gel column chromatography [elution solvent: n-hexane/ethyl acetate = 9/1 - 2/1 (V/V)] to obtain 342 mg (73%) of the title compound in the form of a white solid. 1H-NMR (400MHz, CDCl3) δ: 7.35-7.27 (5H, m), 6.86 (1H, br s), 6.63 (1H, d, J = 3.9 Hz), 6.33 (1H, d, J = 4.3 Hz), 5.87 (1H, s), 5.14 (2H, s), 2.47-2.38 (2H, m), 1.85-1.75 (2H, m), 0.68 (6H, t, J = 7.4 Hz). |