Synthesis of tritium and carbon-14 labelled linoleic acid esters of 3-phenylamino-1,2-propanediol, compounds potentially involved in the etiology of the Toxic Oil Syndrome

Abstract

A simple, one-pot procedure for the preparation of 3H and 14C labelled mono and diesters of fatty acids with 3-phenylamino-1,2-propanediol, compounds shown to have a strong association with Toxic Oil Syndrome, is reported. Ring opening of glycidol with carbon-14 aniline in methanol led to the regioselective insertion of the phenylamino moiety at C-3. This intermediate was allowed to react with the appropriate molar equivalents of tritiated linoleic acid in the presence of DCC and DMAP to give the desired compounds in satisfactory overall yields. © 1998 John Wiley & Sons, Ltd.