Methanol → HCID 131717078, compound

Participants

Reaction Steps

Diphenylmethyl 7β-phenylacetamido-3-[E-2-oxotetrahydrofuran-3-ylidenemethyl)ceph-3-em-4-carboxylate, (0.38 g) in dry dichloromethane (3 mls), cooled to -20° C. under argon, was treated with N-methylmorpholine (0.146 g, 0.158 mls) and a solution of phosphorous trichloride (0.178 g) in dichloromethane (4.4 mls). After 30 mins at -20° C., methanol (5 mls) was added rapidly in one portion. The reaction mixture was allowed to warm slowly to room temperature over 30 mins, and then water (10 mls) added. After vigorous stirring for a further 30 mins the solvents were completely removed in vacuo. The residue was partitioned between ethyl acetate/hexane after adjusting the pH to 8 using aqueous 0.880 ammonia. After washing and drying the organic layer, the solvent was removed and the crude product triturated with ether. Flash chromatography on fine silica gel eluting with ethyl acetate afforded the title compound as a pale yellow foam, (0.116 g, 39%), νmax (CH 2 Cl2) 1780, 1750 and 1720cm-1 ; δH (CDCl3) 2.57-2.72 (1H, m), 2.80-2.96 (1H, m), 3.61 (2H, s), 4.07-4.26 (2H, m), 4.85 (1H, d, J 5.1Hz), 4.98 (1.1Hz), 4.98 (1H, d, J 5.1Hz), 7.04 (1Hz), 7.04 (1H, s) and 7.2-7.5 (10H, m); [mass spectrum: +ve ion (3NOBA, Na+) MNa+ 485].

Provenance & Evidence