Triphenylphosphine → HCID 131710535, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-chloromethyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylate (2.3 g.) in ethyl acetate (20 ml.) was treated with triphenylphosphine (2.3 g., ca. 2 equivs.) and the mixture refluxed for 5 hours. The solution was cooled and the insoluble product isolated by filtration. This material was precipitated from acetone (containing some chloroform) solution by petroleum-ether to give the phosphonium salt (500 mg.) as an amorphous solid [α]D + 68.5° (CHCl3), λmax. (CHCl3) 269.5 and 276.5 nm. (ε 8,880 and 7,620), λmax. (CHBr3) 3440 (NH), 1780 (β-lactam), 1680 and 1510 (--CONH--), and 1445 (P--C aryl) cm.-1, τ(CDCl3) 3.61 (C(2) --H), 4.4 (C(7) --H, dd, J 4.5 and 9 Hz), 4.75 (C(6) --H, not well resolved), 5.04 and 5.18 (CH2 -P, part of two AB-q, JP-H 13 Hz.).

Provenance & Evidence