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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‐ 14 C
Author(s) -
Yoshitake Akira,
Makari Yoshiaki,
Kawahara Kazuo,
Doi Tadashi
Publication year - 1976
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.2580120213
Subject(s) - chemistry , cyclohexane , potassium hydroxide , yield (engineering) , chloroform , potassium cyanide , carbon 14 , cyanide , medicinal chemistry , potassium , ketone , phenol , nuclear chemistry , organic chemistry , materials science , physics , quantum mechanics , metallurgy
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).