m-Chloroperbenzoic acid → HCID 69732331, compound

Participants

Reaction Steps

Finally, T. Aoki et al. (Tetrahedron 1983, 34/15, 2515-2556—in particular pages 2520-2525) disclose the synthesis of diphenylmethyl 7β-(2-thienylacetamino)-3-(1-methyl-1H-tetrazol-5-yl)thiometyl-3-cephem-4-carboxylate, which involves the preparation of diphenylmethyl 7β-(2-thienylacetamino)-3-(l-methyl-1H-tetrazol-5-yl)-3-methylthiocepham-4-carboxylate via the corresponding 3-methylthio-3-chloromethylcepham analog and the reaction of said diphenylmethyl 7β-(2-thienylacetamino)-3-(1-methyl-1H-tetrazol-5-yl)-3-methylthiocepham-4-carboxylate with m-chloroperbenzoic acid in order to remove methylmercaptan and form a 3-(1-methyl-1H-tetrazol-5-yl)-3-cephem structure via the corresponding 1-oxide. However, the method described by Aoki et al. is not transposable to the preparation of third-generation-cefalosporins because the reactants employed affect the amino group which is present on the thiazole ring and is sensitive thereto.

Provenance & Evidence