Ethylene → HCID 10837843, compound

Participants

Reaction Steps

Ethylene was bubbled into a solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethanesulphonyloxy)ceph-3-em-4-carboxylate (0.50 g, 0.852 mmol) in ethyl acetate (500 ml) whilst a solution of diisopropylethylamine (0.15 ml, 0.852 mmol) in ethyl acetate (100 ml) was added dropwise over 2 h. After completion of the addition the mixture was left to stand for 18 h then the solvent was evaporated under reduced pressure. The residue was chromatographed to give the title compound (0.24 g, 61%), (Found: M+, 464.1411. C25H24N2O5S requires M, 464.1406); νmax (CH2Cl2) 1786, 1722, 1686, 1604 cm-1 ; δH (CDCl3) 2.08 (1H, m), 2.46 (1H, dtd, J 10.4, 9.3, 3.2), 3.16 (1H, dtd, J 15.8, 9.4, 1.6), 3.28 (1H, ddt, J 15.8, 8.8, 3.0). 3.63 (2H, ABq, J 16.1), 3.80 (3H, s), 4.32 (1H, dddd, J 9.3, 8.2, 2.8, 1.5), 4.94 (1H, d, J 5.0), 5.18 (2H, ABq, J 11.9), 5.76 (1H, d, J 8.8, 5.0), 5.97 (1H, d, J 8.8), 6.87 (2H, d, J 8.7), 7.26 (7H, m).

Provenance & Evidence