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Syntheses of [2‐ 14 C]penem antibacterials; (FCE 22101 and FCE 22891)
Author(s) -
Fontana Erminia,
Alpegiani Marco,
Perrone Ettore,
Vicario Gian Piero
Publication year - 1987
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.2580240106
Subject(s) - chemistry , yield (engineering) , sodium acetate , sodium , sodium salt , ring (chemistry) , salt (chemistry) , carboxylate , condensation , nuclear chemistry , radiochemistry , organic chemistry , medicinal chemistry , inorganic chemistry , materials science , physics , metallurgy , thermodynamics
The synthesis of FCE 22101 (sodium (5R,6S)‐6‐[(1R)‐hydroxyethyl]‐2‐carbamoyloxymethylpenem‐3‐carboxylate) labelled with carbon‐14 in the 2‐position of the penem system ring was performed in eight steps, using sodium salt of [1‐ 14 C]glycollic acid 1 as the labelled starting material. The final product, penem [2‐ 14 C]FCE 22101 11 , was obtained in an overall radiochemical yield of 21%, 98% radiochemically pure and with a specific activity of 641 MBq/mmol (17.3 mCi/mmol). The acetoxymethyl ester FCE 22891 12 was prepared by condensation of 11 with bromomethyl acetate, with a yield of 41%.