Diethyl Ether → HCID 57240513, compound

Participants

Reaction Steps

A solution of diphenyldiazomethane in ether (prepared from benzophenone hydrazone [21 g, 41.8 mmole]) was added to a solution of 7β-formamido-3-methylceph-3-em-4-carboxylic acid (9.7 g, 40.2 mmole) in tetrahydrofuran (150 ml) and the mixture was stirred overnight in the absence of light. The solvents were removed in vacuo and the residual oil was dissolved in methylene chloride (200 ml). The solution was washed with 3%-sodium hydrogen carbonate solution (2 × 100 ml), dried, and evaporated to a yellow oil which was triturated with ethyl acetate-ether to give the title ester as a white crystalline solid (8.15 g, 49.5%), m.p. 136° to 140°, [α]D23 + 38° (c 0.94; Me2SO), λmax. (EtOH) 258 nm (ε 6,800), νmax. (Nujol) 3330 (NH), 1771 (azetidin-2-one), 1707 (CO2R) and 1655 and 1523 cm-1 (CONH), τ (Me2SO-d6) 1.91 (1H, d, J 9.5 Hz; NH), 1.89 (1H, s; CHO), 2.4 to 2.8 (10H, m; (C6H5)2CH), 3.07 (1H, s; (C6H5)2CH), 3.19 (1H,dd, J 9.5 and 5 Hz; C7 --H), 4.83 (1H,d, 5 Hz; C6 --H), 6.33 and 6.57 (2H, AB-q, 18 Hz; C2 --H2), 7.95 (3H, S; C3 --CH2) (Found: C, 64.55; H, 4.9; N, 6.7; S, 7.7. C22H20N2O4S (408.5) requires C, 64.7; H, 4.9; N, 6.9; S, 7.85%).

Provenance & Evidence