Potassium Carbonate → p-Methoxybenzyl 3-methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylate

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Reaction Steps

3-Methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylic acid (3.48 g., 10 m. moles) was dissolved in dichloromethane (50 ml) with p-methoxy-benzylamine (3.43 g., 25 m. moles) together with anhydrous sodium sulphate (5 g) and potassium carbonate (6.7 g). Nitrosyl chloride (12.5 ml, 10% solution in dichloromethane, 25 m. moles) was added over about 10 minutes at -5° with vigorous stirring. Some partial gel formation occurred but this dissolved while the mixture was stirred for a further 50 minutes while warming towards ambient. The reaction mixture was worked up as described in Example 7 and the organic residue crystallised from hot isopropanol (25 ml) to give the title compound (2.38 g., 50.6% yield based on the input acid) m.pt. 151° - 152°.

Provenance & Evidence