Benzyl chloroformate → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Participants

Reaction Steps

To a solution of 240 g1 L-serine-methylester hydrochloride in 130 ml of water were added at 0° C. 29.8 g of benzyl chloroformate. The pH was kept at 6-7 by adding a 40% aqueous solution of sodium hydroxide. After 3 h at 0° C. the mixture was extracted with 5 portions of ethyl acetate, the combined extracts were dried and evaporated to give 37.12 g (95%) of pure methyl 3-hydroxy-(S)-2-benzyloxycarbonylamino-propionate. IR (neat): 3380m (NH, OH), 1720s, br. (C═O), 1540s (amide II).

Provenance & Evidence