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Synthesis of 1‐([1‐ 14 C] cyclohexyloxycarbonyloxy) ethyl 7β‐[2‐(2‐aminothiazol‐4‐YL)acetamido]‐3‐[[[1‐(2‐dimethylamino‐ethyl)‐1H‐tetrazol‐5‐YL]thio]methyl]ceph‐3‐EM‐4‐carboxylate dihydrochloride ([ 14 C]SCE‐2174)
Author(s) -
Watanabe Masazumi,
Tada Norio,
Imanishi Masayuki,
Yamaoka Masayoshi
Publication year - 1988
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.2580250304
Subject(s) - chemistry , ethyl chloroformate , thio , methyl iodide , cyclohexanol , carboxylate , medicinal chemistry , cefotiam , acylation , potassium carbonate , yield (engineering) , nuclear chemistry , organic chemistry , cephalosporin , catalysis , biochemistry , antibiotics , materials science , metallurgy
1‐(Cyclohexyloxycarbonyloxy)ethyl 7β‐[2‐(2‐amino‐thiazol‐4‐yl)acetamido]‐3‐[[[1‐(2‐dimethylaminoethyl)‐1H‐tetrazol‐5‐yl]thio]methyl]ceph‐3‐em‐4‐carboxylate dihydrochloride (SCE‐2174), a new orally active cephalosporin, was labeled with carbon‐14 starting from [1‐ 14 C]cyclohexanol ( 1 ). 1‐Chloroethyl [1‐ 14 C]cyclohexyl carbonate ( 3 ) obtained by acylation of 1 with 1‐chloroethyl chloroformate ( 2 ) was converted to iodide ( 4 ) which was condensed with the potassium salt of Cefotiam ( 5 ). [ 14 C]SCE‐2174, having a specific activity of 672 MBq/mmol, was obtained in 13% overall radiochemical yield and had a radiochemical purity of 92%.