Synthesis of 2(1H)-Pyrimidinone-Containing α-Amino Acid Derivatives by Chemical Modification of L-Glutamic Acid

A commercially available L-glutamic acid γ-methyl ester was converted into the corresponding urea-containing α-amino acid via the hydrazide, the azide, and then the isocyanate. The condensation of the urea-containing α-amino acid with β-diketones under acidic conditions afforded 2(1H)-pyrimidinone-containing α-amino acid derivatives in reasonable yields. The 1H-NMR analysis of the dipeptide indicated that no detectable racemization had occurred during the chemical modification of L-glutamic acid.