Peracetic Acid → HCID 70479664, compound

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Reaction Steps

To a solution of 3-chloro-7-(imidazol-2-yl)aminocephem-4-carboxylic acid trifluoroacetate as a mixture of delta-2 and delta-3 isomers (157 mg.) in acetic acid (4 ml.) cooled to 10° was dropwise aded peracetic acid (960 μl.) The temperature was allowed to rise to ambient temperature and the mixture was stirred for 2.5 hours. The suspension was filtered to obtain a white solid (27 mg.). The filtrate was evaporated in vacuo and the residue taken up in the minimum amount of a mixture of methanol and CH2Cl2. There was thus obtained a suspension which afforded a crystalline solid on filtration. The solids were combined to give 3-chloro-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylic acid as a mixture of 1α and 1β oxides (61 mg.) containing 0.17 moles of trifluoroacetic acid and having the following n.m.r. spectrum in d6 dimethyl sulphoxide+trifluoroacetic acid: 4.0 and 4.15 (s, 2H); 4.95 and 5.1 (d, 1H);5.7 and 5.8 (d, 1H); 7.05 (s, 2H).

Provenance & Evidence