Pyridine → HCID 70524728, compound

Participants

Reaction Steps

Pyridine (1.2 g.) was added to a solution of phosphorus pentachloride (3.1 g.) in methylene chloride (30 ml.) at 5° to 7° C. and stirred at the same temperature for 30 minutes. To the solution was added 4-nitrobenzyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (5.4 g.) at -10° C., and stirred at the same temperature for 1.5 hours. Methanol (8 ml.) was added to the solution at -30° C. and stirred at 0° C. for 40 minutes. Water (10 ml.) and methylene chloride (50 ml.) were added to the solution and adjusted to pH 5.0 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water (30 ml×2) and adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was evaporated under reduced pressure. The residue was pulverized with diisopropyl ether and the precipitates were collected by filtration to give 4-nitrobenzyl 7-amino-3-acetoxymethylenecepham-4-carboxylate (3.0 g.).

Provenance & Evidence