Triphenylphosphine → HCID 18607841, compound

Participants

Reaction Steps

A solution of triphenylphosphine (1.47 g, 1.5 equiv.) in ethyl acetate (10 ml) was added to a stirred solution of diphenylmethyl 3-bromomethyl-7β-formamidoceph-3-em-4-carboxylate (1.82 g, 3.725 mmole) in ethyl acetate (50 ml). The mixture was stirred overnight at ca. 20° out of direct light, and the precipitated solid was filtered off, washed with ethyl acetate and dried to give the title phosphonium salt (2.41 g, 86%), λmax. (EtOH) 268.5 nm (ε 8,700) and 275.5 nm (ε 8,150), νmax. (CHBr3) 3440 (NH), (1788 azetidin-2-one), 1710 (CO2R), 1680 and 1500 (CONH) and 1443 cm-1 (P+ --C6H5), τ (CDCl3) 1.45 (1H,d, J 9 Hz; NH), 1.73 (1H, s; CHO), 3.57 (1H, s; (C6H5)2CH), 4.32 (1H,dd, J 9 and 5 Hz; C7 --H), 4.62 and 4.78 (2H, centres of 2 AB-quartets, JP-H 16 Hz, JH-H 15 Hz; C3 --CH2P+), 5.12 (1H,d, J 5 Hz; C6 -H), 6.06 and 6.60 (2H, broadened AB-q, J 18 Hz; C2 -H2).

Provenance & Evidence