SYNTHESIS OF N-PI-(2-HYDROXYETHYL)-L-HISTIDINES AND "N-TAU-(2-HYDROXYETHYL)-L-HISTIDINES

Treatment of N2-acetyl-L-histidine methyl ester with ethylene oxide in methanol in the presence of hydrogen chloride and hydrolysis of the products gave N.pi.- and N.tau.-(2-hydroxyethyl)-L-histidine in about equal amounts. Structural assignments of the isomers were based largely on the fragmentation pattern on electron impact of their bis(heptafluorobutyryl) derivatives. The acids are further characterized by their pK'' values, specific rotation and chromatographic behavior.