Acetic Acid → N-(2-Cyanoethyl)-2-methylalanine

Participants

Reaction Steps

Acrylonitrile (5.13 g, 96.9 mmol) was added to a cold (0° C.) solution of 2-amino-2-methylpropanoic acid (10 g, 96.9 mmol) and sodium hydroxide (3.9 g, 96.9 mmol) in water (40 mL) and the resulting mixture was stirred at room temperature for 16 hours. AcOH (6 mL) was added and the precipitate filtered off. The solid was taken up in 95% EtOH (50 mL) and cooled down to 0° C. for 1 hour. The precipitate was filtered off, washed with EtOH (25 mL) and dried to afford the title compound (12 g, 80%) as a white solid. 1H NMR (DMSO-d6) δ 3.37 (s, 1H), 2.70 (t, J=6.3 Hz, 2H), 2.58 (t, J=7.3 Hz, 2H), 1.16 (s, 6H).

Provenance & Evidence