Methanol → HCID 131711748, compound

Participants

Reaction Steps

To a solution of phosphorus pentachloride (3.7 g) in dried dichloromethane (40 ml) at -10° was added N,N-dimethylacetamide (8.25 ml.) and then, slowly, syn-2-(fur-2-yl)-2-methoxyiminoacetic acid (3.00 g), the temperature being kept at approximately -10°. The resulting solution was stirred for 15 minutes, then ice (9 g) was added and the temperature of the solution allowed to rise to 0° over 10 minutes. The organic layer was added to a stirred suspension of diphenylmethyl (1S,6R,7R)-7-amino-3-bromomethylceph-3-em-4-carboxylate 1-oxide, hydrobromide (7.34 g) in dried dichloromethane (100 ml) and propylene oxide (10 ml) at 0°. The reaction mixture was stirred for 45 minutes, during which time it was allowed to warm up to room temperature. To the resulting suspension was added methanol (60 ml) and this mixture was stirred for 10 minutes and then filtered. The white solid was washed with methanol and dried to give the title ester as a white microcrystalline powder (5.26 g, 64%), m.p. 186°-190° (decomp.); [α]D -4.5° (c 1.0, DMSO); λmax (EtOH) 281 nm (ε 22,600). IR and NMR spectroscopy confirmed the structure as that of the title ester.

Provenance & Evidence