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Synthesis of 7‐[α‐(2‐aminothiazol‐4‐yl)‐α‐(z)‐methoximinoacetamido]‐3‐(1‐[ 14 C]methylpyrrolidinio)‐methyl‐3‐cephem‐4‐carboxylate sulfate
Author(s) -
Swigor J. E.,
Pittman K. K.
Publication year - 1987
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.2580240103
Subject(s) - chemistry , formic acid , medicinal chemistry , carboxylate , benzoyl chloride , sodium hydride , sulfoxide , sulfuric acid , chloride , sulfide , inorganic chemistry , organic chemistry , nuclear chemistry
The synthesis of the title compound (6) is described. The reaction of sodium [ 14 C] formate with acetyl chloride produced the mixed anhydride. Treatment with pyrrolidine gave the N‐formyl compound in a 4 to 1 ratio with the N‐acetyl compound. 1 Separation and reduction with lithium aluminum hydride gave N‐[ 14 C]methylpyrrolidine 2 . Reaction with 7‐[α‐(2‐triphenylmethylaminothiazol‐4‐yl)‐α‐(z)‐methoximinoacetamido]‐1‐oxo‐3‐iodomethyl‐3‐cephem‐4‐carboxylate diphenylmethyl ester introduced the label into the cephalosporin. Treatment with acetyl chloride converted the sulfoxide to the sulfide. Formic acid at 39°C removed the protecting groups and treatment with 4N sulfuric acid produced the title compound as a sulfate salt.