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

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)