Methanol → tert-butyl (2S)-2-amino-3-(4-fluorophenyl)propanoate hydrochloride

Participants

Reaction Steps

A stirred solution of ethyl acetate (10 mL) and methanol (0.60 mL, 14.7 mmol) was cooled to 0° C. under an argon atmosphere. Acetyl chloride (1.05 mL, 14.7 mmol) was added dropwise, and the solution warmed to rt and stirred for 30 min. 2-(S)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid tert-butyl ester (Preparation 113, 1 g, 2.95 mmol) was added, and the reaction mixture stirred at rt for 4 h. The reaction mixture was filtered, washed several times with diethyl ether and dried under vacuum to give the title compound. δH (DMSO): 1.30 (9H, s), 3.01 (1H, dd), 3.20 (1H, dd), 4.08 (1H, m), 7.15 (2H, m), 7.32 (2H, m), 8.64 (3H, br s).

Provenance & Evidence