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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
Author(s) -
Guardiola Marisa,
Messeguer Angel
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199801)41:1<75::aid-jlcr60>3.0.co;2-k
Subject(s) - chemistry , glycidol , moiety , regioselectivity , propanediol , methanol , linoleic acid , aniline , organic chemistry , ring (chemistry) , fatty acid , medicinal chemistry , catalysis
A simple, one‐pot procedure for the preparation of 3 H and 14 C 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.