N-(4-methoxybenzyl)-L-tyrosine ethyl ester: Synthesis, structural analysis, and reaction with formaldehyde

This paper describes the structural analysis by single crystal X-ray diffraction (SCXRD) of N-(4-methoxybenzyl)-L-tyrosine ethyl ester; a scorpion-like conformation was revealed between the ethoxycarbonyl group and the 4-hydroxyphenyl group. Zig-zag linear arrangements having head-to-tail intermolecular hydrogen bonds (O-H center dot center dot center dot N) were also observed between N-(4-methoxybenzyl)-L-tyrosine ethyl ester units. It was determined that this amine reacts with formaldehyde to form linear dimers, trimers, and tetramers made up of N-(4-methox-ybenzyl)-L-tyrosine ethyl ester units linked by methylene bridges.