Triphenylphosphine → HCID 88802296, compound

Participants

Reaction Steps

A solution of 2,2,2-trichloroethyl 3-bromomethyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (ca. 7 mmole) in ethyl acetate (25 ml) was stirred at 25° in the absence of light while a solution of triphenylphosphine (3.67g, 2 equiv.) in ethyl acetate (40 ml) was added over 10 minutes. The reaction mixture was stirred at 25° for 31/2 hours and the precipitated solid was filtered off washed with ethyl acetate and dried, (5.62 g), and redissolved in chloroform (40 ml). The filtered solution was diluted with a mixture of ether (20 ml) and light petroleum (b.p. 40 to 60°; 10ml) and stirred for 30 minutes, and the precipitated solid was filtered off and dried to give the title phosphonium salt (5.47 g, 95%), m.p. 125° to 135°, [α]D23 +4.4° (C 1.06; (Me2SO), λmax. (EtOH) 268 nm (ε 9,250) and 275 nm (ε 8,850), νmax. (CHBr3) 3430 (NH), 1794 (azetidin-2-one), 1730 (CO2R), 1693 and 1520 (CONH) and 1442 cm-1 (P+ --C6H5).

Provenance & Evidence