The influence of adjacent phosphate and hydroxyl groups on amino acid esters

Abstract

2-(N-Benzyloxycarbonyl - DL - alanyloxy)-ethanol and 2-DL-alanyloxyethyldihydrogen phosphate have been synthesized. The rates of reaction of the above compounds with hydro-xylamine have been compared with that of DL-alanine methyl ester. Whereas the benzyloxcarbonyl derivative was less reactive, both the glycol monoester and the phosphate were considerably more reactive than the simple ester, the phosphate more so than the glycol monoester. No intermediates were detected during the reaction between the phosphate and aqueous ammonia.