The synthesis of the glucuronide adduct of Trocade

Abstract The synthetic preparation of the glucuronide adduct of Trocade™, a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O -glucuronsyl hydroxylamine ( 9 ) and subsequent coupling to the available carboxylic acid ( 7 ), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade™ occurs on the oxygen of the hydroxamic acid.