Triphenylphosphine → HCID 88802229, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (300 mg.), Rf 0.6 in benzene (5 ml.) was treated with triphenylphosphine (140 mg.) and the total warmed to 50° for 10 minutes. After the mixture had stood at room temperature for a further hour it was diluted with ether and the precipitated solid was collected by filtration. This material was washed thoroughly with ethyl acetate and ether, and on drying in vacuo gave the phosphonium bromide (250 mg.) Rf 0.0 m.p. 135° - 140° C (decomp.) [α]D + 12° (tetrahydrofuran), νmax (CHBr3) 3410 (NH), 1784 (β-lactam), 1710 (CO2R), 1680 and 1515 (CONH) and 1442 (P--C aryl.) cm.-1 τ (CDCl3) 4.38 (C(7) --H, dd, J 4.5 and 9 Hz), 5.19 (C(6) --H, d, J 4.5 Hz), 4.62 and 4.8 (CH2 -- P, two d, JP-H 16 Hz), 6.02 and 6.6 (C(2) -- CH2, two dd, JH-H 18 Hz and JP-H 3-4 Hz).

Provenance & Evidence