Hexane → HCID 54284810, compound

Participants

Reaction Steps

4-Methoxybenzyl (6R,7R)-7-phenylacetamido-3-trifluoromethane-sulphonyloxyceph-3-em-4-carboxylate (0.10 g), bis(dibenzylideneacetone)-palladium (0) (0.003 g) and tri-n-butyl(4,5-dihydrofuran-2-yl)stannane (0.122 g, 0.108 ml ) in dry N-methylpyrrolidinone (0.5 ml) were stirred together for 0.25 h. T.l.c. analysis (50% ethyl acetate--hexane) showed no starting material. The mixture was diluted with ethyl acetate, washed three times with water and with brine and then dried. The solution was concentrated to a small volume and then added dropwise to vigorously stirred hexane (50 ml). The suspension was centrifuged and the clear hexane decanted. The precipitate was washed with hexane and dried in vacuo, to give the title compound as a buff coloured, amorphous solid (0.08 g, 93%); δH (250 MHz, CDCl3) 2.60 (2H, dt, J 9.8, 2.9 Hz), 3.38 and 3.47 (2H, ABq, J 18.1 Hz), 3.60 and 3.96 (2H, ABq, J 16.2 Hz), 3.80 (3H, s), 4.07 (1H, dt, J 18.6, 9.8 Hz), 4.21 (1H, dt, J 17.9, 8.5 Hz), 4.94 (1H, d, J 4.9 Hz), 5.02 (1H, t, 2.9 Hz), 5.17 and 5.23 (2H, ABq, J 12.0 Hz), 5.82 (1H, dd, J 9.1, 4.8 Hz), 6.01 (1H, d, J9.1 Hz), 6.88 (2H, d, J 8.7 Hz) and 7.25-7.41 (7H, m).

Provenance & Evidence