Bulletin of the Chemical Society of Japan

Selective Cleavage of Serine Peptides

T Kaneko, I Takeuchi, T Inui

Index: Kaneko,T. et al. Bulletin of the Chemical Society of Japan, 1968 , vol. 41, p. 974 - 979

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Citation Number: 14

Abstract

The treatment of N-benzyloxycarbonyl-L-alanyl-L-serine methyl ester (I) with phosgene afforded the corresponding O-chlorocarbonyl derivative (II), which was then cyclized to methyl L-3-(N-benzyloxycarbonyl-L-alanyl)-2-oxo-oxazolidine-4-carboxylate (III) accompanied with N-benzyloxycarbonyl-L-alanyl-3-chloro-L-alanine methyl ester (IV) by refluxing in xylene. By the mild alkaline hydrolysis of III, N-benzyloxycarbonyl-L-alanine ...