Studies on the synthesis and resolution of. gamma.-carboxyglutamic acid derivatives

NT Boggs III, B Goldsmith, RE Gawley…

Index: Boggs,N.T. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 2262 - 2269

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Citation Number: 27

Abstract

The synthesis and resolution of N-(benzyloxycarhony1)-y, y-di-tert- butyl-d, ly- carboxyglutamic acid (5a) is described. Resolution using quinine allowed separation of the D enantiomer from the racemic mixture in 15% yield from N-(benzyloxycarbonyl)-0-tosyl-d, l- serine methyl ester (la). Liberation of the L enantiomer from the remaining oily quinine salt followed by purification of the L-tyrosine hydrazide salt of 5a provided an overall yield of ...