Phosphorus trichloride → HCID 67908479, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of diphenylmethyl 3-(6-methyl-2-oxo-2H-pyran-4-ylthio) -7β-phenylacetamidoceph-3-em-4-carboxylate 1-oxide (581 mg) in dichloromethane (5 ml) was cooled in an ice bath and dimethylacetamide (0.25 ml) was added followed by phosphorus trichloride (0.16 ml). The mixture was stirred at 0° C. for 15 mins. and then partitioned between sodium bicarbonate solution and chloroform. The chloroform layer was washed with water, then brine, dried over magnesium sulphate and evaporated. The title compound (509 mg) was isolated by column chromatography of the residue using gradient elution (Kieselgel, 1:1 hexane: ethyl acetate going to neat ethyl acetate). υmax (CHCl3) 3400, 1795, 1725, 1710, and 1680 cm-1. δH (CDCl3) 2.16 (3H, s), 3.33 (1H, d, J 18.1Hz), 3.62 (1H, d, J 17.9Hz), 3.65 (2H, s), 5.03 (1H, d, J 5.1Hz), 5.66 (1H, s) 5.71 (1H, s), 5.94 (1H, dd, J 5.1 and 9.2Hz), 6.96 (1H, s), 6.98 (1H, d, J 9.1Hz), 7.2-7.4 (15H, m). [mass spectrum: +ve ion (3 NOBA, Na+) M Na+ 647].

Provenance & Evidence