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ChemInform Abstract: Direct O-Acylation of Small Molecules Containing CO- 2---HN··←HO Units by a Distorted Amide: Enhancement of Amine Basicity by a Pendant Carboxylate in a Serine Protease Mimic.
First published: May 30, 1989
Abstract
The kinetics of the reaction of two series of amino alcohols (imidazoles such as (I); ethanolamines such as (III)) with a distorted amide (anilide (II)) are studied as models for the acylation of the serine proteases.
ChemInform Abstract
The kinetics of the reaction of two series of amino alcohols (imidazoles such as (I); ethanolamines such as (III)) with a distorted amide (anilide (II)) are studied as models for the acylation of the serine proteases. In all cases, the reactions proceed by initial O-acylation to produce esters such as (IV). With prim. or sec. ethanolamines, subsequent O→N acyl transfer occurs to give amides such as (V).
