Triphenylphosphine → HCID 88802324, compound

Participants

Reaction Steps

A solution of triphenylphosphine (1.95 g, 2 equiv.) in ethyl acetate (6 ml) was added to a solution of t-butyl 3-bromomethyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (1.80 g, 3.72 mmole) in ethyl acetate (4 ml.). The mixture was stirred for 1 hour, and the precipitated solid was filtered off, washed with ether and dried to give the title phosphonium salt (2.42 g, 87.5%), m.p. 144° to 146°, [α]D22 +31° (C 0.95; Me2SO), λmax. (EtOH) 268 nm (ε 11,300) and 275 nm (ε 10,400), νmax. (Nujol) 3400 (NH), 1778 (azetidin-2-one), 1692 and 1520 (C0NH), 1690 (CO2R) and 1430 cm-1 (P+ -C6H5), τ (Me2SO-d6) 0.89 (1H, d, j 8 Hz; NH), 2.66 and 2.99 (2H and 3H, 2 m; C6H5O), 4.29 (1H, centres of two AB-quartets, JH-H 15 Hz, JP-H 16 Hz; C3 -CH2P+), 5.33 (2H, s; C6H5OCH2), 8.76 (9H, s; CO2C(CH3)3).

Provenance & Evidence