Synthesis of Heterocyclic β-Amino Acids. A Convenient Preparation of β-Amino-5-Pyrimidinepropanoic Acid and Derivatives.

Article abstract of DOI:10.1016/S0040-4039(00)61438-7

The novel (2E)-1,1-dimethylethyl-3-(5-pyrimidinyl)-2-propenoate 3, obtained by Heck coupling between 5-bromopyrimidine and tert-butyl acrylate undergoes nearly quantitative Michael addition in t-butanol saturated with ammonia to the hitherto unknown β-amino-5-pyrimidinepropanoic ester 4.The synthetic utility of this reactions sequence is demonstrated by preparation of 4 on a multigram scale.The transformation of the ester to the free amino acid 5 and to the Cbz-N-protected amino acid 7 is described.The tert-butyl ester 4 and N-protected β-amino acid 7 are useful in peptide and peptidomimic synthesis.