Modified tert-butoxycarbonyl(m-BOC) derivatives as monomeric and polymeric aminoprotecting groups — VII

Abstract Polymerizable N-methacrylamino m -BOC-type 1,1-dimethyl-2-methacrylmethanamido-ethoxy-carbonyl- and 1,1-dimethyl-3-methacrylmethanamido-butoxy-carbonyl group, derived from the corresponding t -alkohols have been developed as acid labile aminoprotecting groups. The synthesis of monomeric and polymeric N-methacrylamino m -BOC amino acids and amino acid methyl esters and their application for peptide synthesis following the (N→C)-assembly method are described. The rapid, acid induced cleavage of the protecting group leads to the formation of oxazole resp oxazine derivatives.