Helvetica chimica acta

A New 2H??Azirin??3??amine as a Synthon for α??Methyl Glutamate

FM Hilty, KA Brun, H Heimgartner

Index: Hilty, Florentine M.; Brun, Kathrin A.; Heimgartner, Heinz Helvetica Chimica Acta, 2004 , vol. 87, # 10 p. 2539 - 2548

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Citation Number: 9

Abstract

Abstract The synthesis of a novel 2, 2-disubstituted 2H-azirin-3-amine 10 as a building block for racemic Glu (2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S-acid and the amino acid Z-Val-OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively (Scheme 2). From 18, each of the protecting groups was removed selectively (Scheme 3).