Premium
Synthesis of cefepime‐d 3 and cefepime‐d 8
Author(s) -
Kamachi Hajime,
Okita Takaaki,
Tsuno Takashi,
Naito Takayuki
Publication year - 1990
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.2580281015
Subject(s) - chemistry , cefepime , pyrrolidine , methyl iodide , cephem , sodium iodide , iodide , acylation , carboxylate , hydrochloride , salt (chemistry) , medicinal chemistry , organic chemistry , carboxylic acid , antibiotics , catalysis , biochemistry , antibiotic resistance , imipenem
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 .