Trisodium citrate → HCID 131721627, compound

Participants

Reaction Conditions

Reaction Steps

4-Methoxybenzyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-(Z)-pent-2-enamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (80 mg) in dichloromethane (2 ml) was added dropwise to a mixture of aluminium chloride (47 mg) and anisole (1.03 ml) in dichloromethane (2 ml) at -50° C. under argon. The mixture was stirred for 15 minutes at -40° C. and 0.5M trisodium citrate (3.42 ml) added, stirred at room temperature for 15 minutes then diluted with dichloromethane (10 ml) and water (10 ml). The aqueous layer was collected, washed with dichloromethane and chromatographed on HP20SS eluting with 0, 1, 2, 5 and 10% acetone in water. Fractions containing the product, h.p.l.c analysis, were combined, concentrated and freeze-dried to give the title compound (22 mg); νmax (KBr) 3407, 1757, 1609, 1527, 1375, 1338 and 1041 cm-1 ; δHD2O, 250 MHz) 1.03 (3H,t,J 7.5 Hz), 1.65-2.30 (6H,m), 3.32 and 3.51 (2H, ABq, J 7.7 Hz), 3.70-3.95 (2H,m), 4.65-4.80 (1H,m), 5.20 (1H,d,J 4.7 Hz), 5.74 (1H,d,J 4.7 Hz), 6.33 (1H,t,J 8 Hz) and 6.47 (1H,s). [Mass spectrum +ve ion (thioglycerol) MH+ (473)].

Provenance & Evidence