Hydrochloric Acid → Benzhydryl 7-[2-(6-aminopyridin-2-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate

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To a solution of benzhydryl 7-[2-(6-formamidopyridin-2-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.5 g) in methanol (100 ml) and tetrahydrofuran (25 ml) was added conc. hydrochloric acid (1.5 ml). The solution was stirred for 90 minutes at 30° to 35° C. The resultant solution was adjusted to pH 5.0 with a saturated aqueous solution of sodium bicarbonate and then methanol was evaporated under reduced pressure. The residual oil was dissolved in ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give benzhydryl 7-[2-(6-aminopyridin-2-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.4 g), mp. 121° to 128° C. (dec.).

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