Methyl chloroformate → Methyl 2-bromo-N-(methoxycarbonyl)-D-phenylalaninate

Participants

Reaction Steps

Dissolve methyl 2-bromo-D-phenylalaninate hydrochloride (27.2 g, 92.3 mmol) in dichloromethane (923 mL) and water (185 mL). Add sodium bicarbonate (31.0 g, 369.4 mmol) and methyl chloroformate (7.86 mL, 101.6 mmol) at room temperature. Stir the mixture 2.5 hours. Dilute with water and extract with dichloromethane. Dry the dichloromethane extracts over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography eluting with ethyl acetate:hexanes (10-75% gradient) to give the title compound (29.1 g, 92.1 mmol). MS (m/z): 316 (M+1).

Provenance & Evidence