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Synthesis of [14C]E1077, a novel parenteral cephalosporin antibiotic

✍ Scribed by Yasunobu Kai; Shigeru Chiku

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
195 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

(−)‐(RS)‐(E)‐3‐[(6R,7R)‐7‐((Z)‐2‐(5‐amino‐1,2,4‐thiadiazol‐3‐yl)‐2‐fluoromethoxyiminoacetamide]‐2‐carboxy‐8‐oxo‐5‐thia‐1‐azabicyclo[4.2.0]oct‐2‐ene‐3‐yl‐2‐propenyl ethylmethylammonium hydroxide inner salt (E1077), a new parenteral cephalosporin with well‐balanced antibacterial spectrum and potent antibacterial activity, was labelled with carbon‐14, starting from potassium [^14^C]thiocyanate which on reaction with (Z)‐2‐(N‐chloroamidino)‐2‐fluoromethoxyiminoacetic acid (I) gave(Z)‐2‐(5‐amino‐1,2,4‐[5‐^14^C]thiadiazol‐3‐yl)‐2‐fluoromethoxyiminoacetic acid (II).

(RS)‐(E)‐3‐‐7‐Amino‐2‐carboxy‐8‐oxo‐5‐thia‐1‐azabicyclo[4.2.0]oct‐2‐ene‐3‐yl‐2‐propenyl ethylmethylammonium hydroxide inner salt (III) was acylated with the above acid using the POCl~3~‐DMF method, to afford the title compound (IV); [^14^C]E1077, having a specific activity of 3.36 MBq/mg, was obtained in 50.3% overall radiochemical yield, with a radiochemical purity of more than 97.1%.

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