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Synthesis of (6R,7R)-7-[2-(5-aminio-1,2,4-[5-14C]thiadiazol-3-yl)-(Z)-2-methoxyimiyiminoacetamido]-3-[(4-carbamoyl-1-quinuclidinio)methyl]ceph-3-em-4-carboxylate([14C]E1040)

✍ Scribed by Isao Sugiyama; Seiichirou Nomoto; Hitoshi Mizuo; Hiroshi Yamauchi

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
176 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

(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%.

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