N-carbobenzyloxyalanine → HCID 86734612, compound

Participants

Reaction Steps

In a manner analogous to that given in Example 13 (a), from the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine and dimethyl 1-aminobenzylphosphonate hydrochloride, there was obtained an isomeric mixture. After chromatography on silica gel with an isopropanol/ethyl acetate eluant, followed by recrystallization from ethyl acetate/ether, there were isolated dimethyl (1S)-1-[(N-benzyloxycarbonyl-L-alanyl)-amino] -benzylphosphonate of melting point 103°-105° C [[α]D20 =- 46.6°(c = 1% in methanol)]and dimethyl (1R)-1-[(N-benzyl-oxycarbonyl-L-alanyl)]-benzylphosphonate of melting point 120°-122° C [[α]D20 =+ 12.3°(c = 1% in methanol)]

Provenance & Evidence