Synthesis of erythro-L-β-Hydroxyglutamic Acid Hydrochloride from L-Malic Acid

Abstract

Facile synthesis of erythro-L-β-hydroxyglutamic acid and its derivative, (2S, 3S)-3-acetoxypyroglutamate, from L-malimide is described. The Key reaction for the synthesis of 3-oxypyroglutamyl intermediate was the furylation of N-acylaminal acetate using zinc bromide-trimethylchlorosilane as an effective catalyst system. Oxidative cleavage of the furyl substituent afforded the 3-acetoxypyroglutamate, which on hydrolysis gave the title amino acid.