Study of the effect of the nature of the side chain in esters of alpha-amino acids on the diastereoselectivity of condensation with 5(4H)oxazolone in the synthesis of dipeptides with N-terminal N-acetylphenyIalanine

摘要

Conditions for fast racemization of 5(4H)-oxazolones prepared from N-acylphenylalanine were found.Reactions of 4-benzyl-2-methyl-5(4H)-oxazolone with amino acid esters proceed diastereoselectively to give predominantly dipeptides comprising R-phenylalanine.The diastereoselectivity increases with complication of the structure of the side chain in the amino acid esters.