A selective method for the preparation of primary amides: Synthesis of Fmoc-L-4 carboxamidophenylalanine and other compounds

Article abstract of DOI:10.1016/S0040-4039(99)00245-2

A new method for the synthesis of primary amides was developed in which carboxylic acids were treated with ammonium chloride in the presence of peptide synthesis coupling agents and base at room temperature. These mild conditions allow the conversion of carboxyl groups to primary amides on substrates possessing sensitive functional groups such as esters and the base-labile Fmoc protecting group.