A novel, one-pot preparation of N-methyl-α-amino acid dipeptides from oxazolidinones and amino acids

Abstract

A new synthetic method has been developed to prepare N-methyl dipeptides in one-pot directly from oxazolidinones. Treatment of oxazolidinone 1 with an amino ester yields an intermediate N-hydroxymethyl dipeptide 3, which is treated with TFAA and triethylsilane to give N-methyl dipeptide 6 in good yield. The reaction parameters which were explored include the rate of oxazolidinone ring opening, the stability of 3, and the optimum solvent and acid for conversion of 3 to 6.