Beta-Alanine → N-Benzyloxycarbonyl-beta-alanine

Participants

Reaction Steps

A stirred solution of β-alanine (50.10 g, 0.562 mol) in 2M NaOH (281 mL) at 0° C. was treated with benzyl chloroformate (88 mL, 1.1 equiv), dropwise over 1 h. Stirring was continued for 1.5 h at 0° C., followed by 1.5 h at rt. The resulting mixture was extracted with ether (4×500 mL). The aqueous phase was acidified with 5M HCl (120 mL). The resulting white precipitate was collected by filtration, washed with water and dissolved in methylene chloride. The solution was dried over sodium sulfate and concentrated in vacuo to give a white solid (114.95 g, 92%). 1H-NMR (CDCl3) 6 2.61 (t, 2H), 3.48 (q, 2H), 5.12 (s, 2H), 5.29 (br, 1H), 7.37 (s, 5H). MS (DCl) 224 (MH)+.

Provenance & Evidence