Semisynthetic cephalosporins with .Alpha.-oximino acid side chains. The preparation and coupling of 4-acylamino-.Alpha.-oximinobenzeneacetic acids and 1,2-dihydro-6-methyl-.Alpha.-oximino-2-oxo-3-pyridineacetic acid to 7-aminocephalosporanic acid

Domagala, J.M.; Haskell, T.H.; Showalter, H.D.H.

The Journal of Antibiotics 34(11): 1447-1455


DOI: 10.7164/antibiotics.34.1447
Accession: 068515921

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A series of 4-acylamino-alpha-oximinobenzeneacetic acids, and 1,2-dihydro-6-methyl-alpha-oximino-2-oxo-3-pyridineacetic acid were prepared and coupled to 7-aminocephalosporanic acid and its 3'-(1-methyltetrazol-5-yl)thiolo analogue. Several coupling methods and oxime protecting groups were thoroughly examined. The best coupling procedure employed dimethylchloroformiminium chloride, and the tetrahydropyranyl (THP) group was selected for oxime protection. The cephalosporins prepared were tested and compared to cefuroxime and cefotaxime. The corresponding alpha-keto acids, and O-methyl oximes were also examined.