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Synthesis of (6R,7R)‐7‐[2‐(5‐aminio‐1,2,4‐[5‐ 14 C]thiadiazol‐3‐yl)‐(Z)‐2‐methoxyimiyiminoacetamido]‐3‐[(4‐carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate([ 14 C]E1040)
Author(s) -
Sugiyama Isao,
Nomoto Seiichirou,
Mizuo Hitoshi,
Yamauchi Hiroshi
Publication year - 1991
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.2580291207
Subject(s) - chemistry , hydrochloride , yield (engineering) , potassium thiocyanate , acetic acid , acetic anhydride , carboxylate , medicinal chemistry , chloride , thiocyanate , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
(6R,7R)‐7‐[2‐(5‐amino‐1,2,4‐thiadiazol‐3‐yl)‐(Z)‐2‐methoxyiminoacetamido]‐3‐[4‐(carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate (E1040), a new injectable cephalosporin with potent antipseudomonal activity, was synthesized labelled with carbon‐14, starting from potassium [ 14 C]thiocyanate with 2‐(N‐chloroamidino)‐2‐(methoxyimino)acetic acid (I) gave (5‐amino‐1,2,4‐[5‐ 14 C]thiadiazol‐3‐yl‐2‐methoxyimino)acetic acid (II). 7‐Amino‐3‐[(4‐carbamoyl‐1‐quinuclidinio)methyl]ceph‐3‐em‐4‐carboxylate hydrochloride (IV) was acylated with the above acid chloride using the PCl 5 method, to afford the title compound (V); [ 14 C]E1040, having a specific activity of 3.74 MBq/mg (as its anhydride), was obtaind in 47% overall radiochemical yield, with a radiochemical purity of more than 98.1%.