A Simple Method for the Synthesis of Long-Chain Alkyl Esters of Amino Acids

Article abstract of DOI:10.1021/jo00209a018

A practical one step procedure is described for the synthesis of long-chain alkyl esters of amino acids.A number of octadecyl (stearyl) amino acids were made in moderate to high overall yields of 40-90percent via methanesulfonic acid catalyzed esterification in an octadecanol melt.No special anhydrous conditions or N-protected amino acids were required and so in the case of lower product yields the synthesis was still desirable relative to alternative methodologies.Further, simpler routes gave lower yields.A correlation was observed between reactant hydrophilicity and product yields.