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Synthesis of 7-[α-(2-amino-[2-14C]thiazol-4-yl)-α-(Z)-methoxyiminoacetamido]-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate hydrochloride ([14C]cefepime hydrochloride)

✍ Scribed by R. T. Standridge; J. E. Swigor

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
289 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The title compound 9 was prepared by the route outlined in Scheme I. [^14^C]Thiourea (1) was condensed with ethyl 4‐bromo‐3‐oxo‐2‐methoxyiminoacetate (2), providing ethyl 2‐(2‐amino‐4‐[2‐^14^C]thiazolyl)‐2‐methoxyiminoacetate (3), as the pure Z‐isomer. Saponification gave the amino acid 4; this was reacted with 1‐hydroxybenzotriazole to give the activated ester 5. Condensation in situ with 7‐amino‐3‐(1‐methylpyrrolidinio) methyl‐3‐cephem‐4‐carboxylate (6) yielded the product as the pure sulfate salt (7).

Treatment of 7 with base provided the zwitterion 8, isolated as the stable N‐methyl‐2‐pyrrolidinone adduct. An aqueous solution of the adduct was converted to the crystalline title compound, [^14^C]Cefepime hydrochloride hydrate (9), with hydrochloric acid/acetone. Radiochemical purity was 99.0% and specific activity, 34.2 μCi/mg. Overall yield from [^14^C]thiourea was 18%.

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