Pyridine → HCID 13591262, compound

Participants

Reaction Conditions

Reaction Steps

0.4 ml (5 mmols--2.5 equivalents) of pyridine and then, all at once, 0.83 g (4 mmols--2 equivalents) of phosphorus pentachloride were added to a solution, cooled to -20° C., of 749 mg (2 mmols) of tert.-butyl (6R, 7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate in 3.7 ml of anhydrous methylene chloride. The mixture was stirred at 0° C. for 10 minutes and at +15° C. for 1 hour and cooled to -60° C., 12.2 ml of precooled anhydrous methanol were added rapidly and the mixture was subsequently stirred at room temperature for 30 minutes. It was then cooled to -15° C., 1.6 ml of distilled diethylamine was added and stirring was continued for 10 minutes at about -10° C. and the mixture was poured into ice-cold saturated NaHCO 3 solution, for working up. The mixture was extracted several times with methylene chloride and the extract was washed with water and dried over MgSO4. The solvent was evaporated off in vacuo and the residue was chromatographed on 60 g of silica gel (ethyl acetate:acetone 85:15). 158 mg (29%) of the title compound were obtained as a light rigid foam, RF : 0.33 (ethyl acetate:acetone 85:15).

Provenance & Evidence