Pyridine → Benzhydryl 7-amino-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate

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Reaction Steps

Pyridine (0.39 ml) was added to a suspension of phosphorus pentachloride (1.01 ml) in dry methylene chloride (25 ml) at 5° C., and the mixture was stirred at ambient temperature for 30 minutes. Benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate (2.5 g) was added to the above mixture at -10° C. and stirred for two-hours. Then, methylcellosolve (2.3 ml) was added to the reaction mixture at -30° C. and the resulting solution was stirred for an hour. To the above solution was added 5 ml of water and the separated organic layer was washed in turn with a saturated aqueous solution of sodium bicarbonate and brine, dried. The solvent was evaporated to give benzhydryl 7-amino-3-(2,2-dibromovinyl)-3-cephem-4-carboxylate (1.7 g).

Provenance & Evidence