Methanol → HCID 67923927, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylmethyl 7β-phenylacetamido-3-(E-phthalidylidenemethyl)ceph-3-em-4-carboxylate (1.3 g), dissolved in dichloromethane (10 mls) was cooled to -20° C. under argon. N-methylmorpholine (0.5ml) followed by a solution of phosphorous pentachloride (0.561 g) in dichloromethane (15 mls) were then added. After ca 30 mins, i.r. analysis showed no starting material. Dry methanol (10 mls) was added in one portion very rapidly, and the solution allowed to warm to room temperature over 30 mins. Water (20 mls) was added and the mixture vigorously stirred for 20-30 mins. After washing and drying the organic phase, the crude product was purified by flash chromatography, eluting with 70 and 80% ethyl acetate/hexane. The title compound was obtained as a pale yellow solid, (0.563 g, 53%), νmax (CH2Cl2) 1780(s), 1720, 1600(w,br), 1560 and 1210cm-1 ; δH (CDCl3) 3.56 (2H,ABq,J18.7Hz), 4.93 (1H,d,J5.1Hz), 5.10 (1H,d,J5.1Hz), 6.39(1H,s), 6.88 (1H,s), 7.21 (10H,m), 7.46-7.68 (3H,m), and 7.87 (1H,d,J7.6Hz); [mass spectrum: +ve ion (3-NOBA, Na+) M Na+, 532].

Provenance & Evidence