Benzyl chloroformate → N-carbobenzyloxy-beta-chloro-L-alanine

Participants

Reaction Conditions

Reaction Steps

To 86.19 g of an aqueous solution containing 7.47 g of β-chloroalanine was added 11.35 g of benzyloxycarbonyl chloride (1.1 moles per mole of β-chloroalanine) dropwise over 1 hour under constant stirring at about 5° C., with the reaction system being maintained at pH 9.7 with a 30% aqueous solution of sodium hydroxide. The reaction was further continued for 3 hours, at the end of which time the reaction mixture was washed with 50 ml of toluene. This washed reaction mixture, 89.53 g, contained 15.52 g (yield 100%) of N-benzyloxycarbonyl-β-chloroalanine.

Provenance & Evidence