Tributylphosphine → HCID 70616310, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-iodomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (4.9 g.) in ethyl acetate (90 ml.) was stirred in the dark at room temperature and treated, over 15 minutes, with a solution of tri-n-butylphosphine (3.1 g., ca. 2 equivs.) in ethyl acetate (50 ml.). The solution was stirred for a further 45 minutes and precipitated into petroleum-ether to give the phosphonium iodide (3.448 g.), m.p. 120°-125° (decomp), [α]D - 43°(N,N-dimethylformamide), RF 0.0, inflexion (EtOH) at 259 nm. (ε 7,100), νmax. (CHBr3) 3410 (-NH), 1786 (β-lactam), 1708 (ester), and 1686 and 1510 cm. -1 (-CONH-), τ (CDCl3) 4.22 (C(7) -H, dd, J 5 and 9 Hz.), 4.87 (C(6) -H d, J 5 Hz), 5.80 and 6.11 (C(2) -CH2, two dd, JH-H 18 Hz., JP-H 3-4 Hz). [Found: C, 55.3; H, 6.0; I, 15.7; N, 3.1; P, 3.7 C39H50IN2O4PS2 (832.8) requires C, 56.2; H, 6.1; I, 15.1; N, 3.4; P, 3.7%].

Provenance & Evidence