3-Aminopyridine → HCID 88719081, compound

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Reaction Steps

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-1, 738 mg, 0.8 mmole) and 3-aminopyridine (113 mg, 1.2 mmole) in methylene chloride (15 ml) was stirred at room temperature for 1.5 hours and then concentrated under reduced pressure. The residue was triturated with diisopropyl ether and treated with a mixture of 90% trifluoroacetic acid (TFA) (8 ml) and anisole (1.6 ml) at room temperature for 1 hour, and then was concentrated and triturated with ether. The resulting crude product was purified by column chromatography using HP-20 (eluted with 10% methanol and 30% methanol) and the packing in a PrepPAK-500/C18 cartridge (Waters) (eluted with 5% methanol). The desired fraction was concentrated and lyophilized to give 38 mg (9%) of the title compound (I-1E). Estimated purity, 55%. M.p. >170° C. (dec.).

Provenance & Evidence