N-alkoxycarbonyl amino acid N-carboxyanhydrides and N,N-dialkoxycarbonyl amino acid fluorides from N,N-diprotected amino acids

Abstract

Activation of N,N-bis-Boc or N-Boc N-Z amino acids with SOCl2–DMF leads to N-protected N-carboxy amino acid anhydrides, whereas treatment with cyanuric fluoride at low temperature gives mainly N,N-bis-protected amino acid fluorides, which are efficient acylating agents.