A simple method for the synthesis of long-chain alkyl esters of amino acids

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 40-90% 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.