Hydrochloric Acid → (S)-Benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:18][NH:19][O:20][CH3:21].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:14](=[O:16])[N:19]([O:20][CH3:21])[CH3:18])[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-Benzyloxycarbonyl-L-alanine (6.5 g, 28.5 mmol), N,O-dimethylhydroxylamine hydrochloride (3.4 g, 36.2 mmol), and N-hydroxybenzotriazole (4.8 g, 34.8 mmol) were dissolved in THF (32 mL) and cooled to 0° C. under N2. Diisopropylethylamine (12.3 mL, 71.3 mmol) was slowly added, maintaining the temperature below 25° C. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.0 g, 36.2 mmol) was then added slowly, maintaining the temperature at 15-25° C. The slurry was stirred overnight at room temperature, and then cooled to 0° C. 1N Aqueous HCl (36 mL) was added slowly, and the mixture was warmed to room temperature and extracted with EtOAc. The combined organic layers were washed with 10% aqueous HCl, saturated aqueous NaHCO3, and brine, and then concentrated and purified by silica gel chromatography to give the title compound.
Workup
- temperaturemaintaining the temperature below 25° C
- temperaturemaintaining the temperature at 15-25° C
- temperaturecooled to 0° C
- temperaturethe mixture was warmed to room temperature
- extractionextracted with EtOAc
- washThe combined organic layers were washed with 10% aqueous HCl, saturated aqueous NaHCO3, and brine
- concentrationconcentrated
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-8b77a72f37234a2cb9dd59b5298d6c5f
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497381B2
Reaction notes
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