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Synthesis of cefepime-d3 and cefepime-d8

✍ Scribed by Hajime Kamachi; Takaaki Okita; Takashi Tsuno; Takayuki Naito

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
242 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Synthesis of cefepime‐d~3~ (6a) and cefepime‐d~8~ (6b) is described. Diphenylmethyl 7‐benzylideneamino‐3‐chloromethyl‐3‐cephem‐4‐carboxylate (2) was treated with sodium iodide to afford the iodide 3, which was, without isolation, allowed to react with N‐methyl‐d~3~‐pyrrolidine to give the quarternary salt 4a. Deblocking of 4a with HCO~2~H and HCl gave 7‐amino‐3‐(N‐methyl‐d~3~‐pyrrolidinio)methyl‐3‐cephem‐4‐carboxylate hydrochloride (5a). Acylation of 5a with benzotriazol‐1‐yl (Z)‐2‐(2‐aminothiazol‐4‐yl)‐2‐methoxyiminoacetate followed by treatment with dil. H~2~SO~4~ afforded 6a sulfate. In the same way, 6b was synthesized using N‐methyl‐pyrrolidine‐d~8~.

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