Transacetylation Reaction of Possible Enzymatic Significance

Abstract

TREATMENT of N-salicoylethanolamine (1) with acetic anhydride in the presence of aqueous sodium hydroxide (1 mol.) at 0° has been found to yield small amounts of N-salicoyl-O-acetylethanolamine (7) and O-salicoyl-N-acetylethanolamine (4) in addition to the expected N-(O-acetylsalicoyl)-ethanolamine (2) and unchanged starting material. The mixture could be resolved by thin-layer chromatography on ‘Kieselgel G’ using the solvent system benzene–methanol–acetic acid (45 : 8 : 4 v/v). Compounds (1), (4) and (7) gave a blue colour on spraying with ferric chloride solution while compound (2) gave no colour initially but developed a strong blue colour on standing. Compound (2) readily undergoes rearrangement and has not so far been obtained in an analytically pure state. Its structure, however, follows from its conversion into a trityl derivative identical with the product obtained by acetylation of N-salicoyl-O-tritylethanolamine.