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A facile synthetic route to the 14 C‐labeled enantiomers of MK‐196, A new uricosuric diuretic, and its major metabolite
Author(s) -
Woltersdorf Otto W.
Publication year - 1980
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/jlcr.2580170505
Subject(s) - chemistry , metabolite , enantiomer , alkylation , acetic acid , ether , hydrochloride , diuretic , derivative (finance) , pyridine , saponification , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , medicine , financial economics , economics , endocrinology
The enantiomers of MK‐196, (6,7‐dichloro‐2‐methyl‐1‐oxo‐2‐phenyl‐5‐indanyloxy)‐acetic acid, and the 2‐(4‐hydroxyphenyl) derivative, the major metabolite of MK‐196, were resolved by classical methods using α‐methylbenzylamine salts, and converted to the corresponding, enantiomerically pure (indanyloxy)acetic acids‐α‐ 14 C by facile ether cleavage with pyridine hydrochloride to the 5‐indanols, selective O‐re‐alkylation with methyl bromoacetate‐2‐ 14 C and subsequent saponification.