The synthesis of the glucuronide adduct of Trocade™

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.