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Labelling of a new hypolipaemic agent with carbon-14, preparation of 1,1-bis[4-(1-carboxy-1-methylpropoxy)phenyl]cyclohexane-2-14C

✍ Scribed by Akira Yoshitake; Yoshiaki Makari; Kazuo Kawahara; Tadashi Doi

Publisher
John Wiley and Sons
Year
1976
Tongue
French
Weight
442 KB
Volume
12
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1,1‐Bis[4‐(1‐carboxy‐l‐methylpropoxy)phenyl]cyclahexane (S‐8527) (I), a new hypolipaemic agent, was labelled at C‐2 with carbon‐14 for the use of metabolic studies. The procedure used is illustrated in Fig. 1. Cyclohexane‐2‐^14^C which was prepared from potassium cyanide‐^14^C was condensed with phenol to afford 1,1‐bis(4‐hydroxyphenyl)cyclohexane‐2‐^14^c (VI). Condensation of VI with ethyl methyl ketone and chloroform under a strong base (potassium hydroxide) gave S‐8527‐2‐^14^C (I). A total of 3.11 mCi of pure S‐8527‐2‐^14^C (I) was obtained, representing 12% radiochemical yield from potassium cyanide‐^14^C. Furthermore, a new radioactive by‐product was isolated and elucidated its structure as X (Fig. 3).

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