反应详情

A solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethyl-sulphonyloxy)ceph-3-em-4-carboxylate (40 mg, 0.0682 mmol) in dichloromethane (5.0 ml) was cooled to -20° C. Trans-2-butene (ca. 5 ml) was condensed into the solution. Diisopropylethylamine (12 μl, 0.068 mmol) was added and the mixture allowed to warm to room temperature over 1 h. The mixture was chromatographed to give the title compound (29.7 mg, 88%), m.p. 172°-173° C. (EtOAc) (Found: C, 65.6; H, 5.5; N, 5.6; S, 6.2; M+, 492.1724. C27H28N2O5S requires C, 65.8; H, 5.7; N, 5.7; S, 6.5%; M, 492.1719; νmax (CH2Cl2) 1786, 1721, 1687 cm-1 ; δH (CDCl3) 1.03 (3H, d, J 7.1), 1.25 (3H, d, J 7.3), 2.41 (1H, ddq, J 9.5, 7.1, 3.0), 3.04 (1H, ddq, J 7.3, 3.2, 3.0), 3.63 (2H, ABq, J 16.0), 3.79 (3H, s), 4.47 (1H, dd, J 9.5, 3.2), 4.90 (1H, d, J 4.9), 5.08 (1H, d, J 11.9), 5.26 (1H, d, J 11.9), 5.76 (1H, dd, J 9.0, 4.9), 6.07 (1H, d, J .9.0), 6.87 (2H, d, J 8.7), 7.30 (7H, m); δc (CDCl3), 15.9, 17.9, 37.2, 43.1, 43.4, 47.0, 55.3, 58.3, 59.8, 67.0, 114.0 (2c), 130.5 (2c) 121.7, 127.4, 127.7, 129.1 (2c), 129.5 (2c), 130.5 (2c), 133.8, 142.9, 159.8, 160.8, 164.2, 171.2

1. customcondensed into the solution
2. customThe mixture was chromatographed