The selective stepwise chemical hydrolysis of alkylcarbonate groups from novel mixed alkylcarbonate trialkyl ester derivatives of etidronic acid

Abstract

The chemical hydrolysis behaviour for etidronic acid trialkyl alkylcarbonate derivatives (3a–d) has been studied. Selective quantitative degradation of alkylcarbonate groups from the phosphorus end over the hydrolysis of an alkylcarbonate group in a tertiary hydroxyl group of etidronic acid has been reported. Further selective hydrolysis of the alkoxycarbonyl group from the tertiary hydroxyl group over the hydrolysis of ester groups was observed and this represented a novel method to the synthesis of trialkyl esters of etidronic acid (4c,d) with very reasonable 38% (4c) and 43% (4d) overall yields.