Chloroform → HCID 131710537, compound

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Reaction Steps

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (583 mg.) in ethyl acetate (5 ml.) was treated with a solution of tri-n-butylphosphine (0.3 ml., ca. 2 equivalents) in ethyl acetate (2 ml.). After 10 minutes at room temperature the mixture was diluted with petroleum ether to give the phosphonium salt (690 mg.) as an amorphous solid, m.p. 65° - 70° [α]D23 - 35° (c 1.0 CHCl3), inflexion at 237 nm. (ε 12,460) and 258 nm. (ε 6,550), νmax 1770 (β-lactam), 1702 (CO2R), 1670 and 1530 (CONH) and 693 (phenyl) cm.-1 ; τ (CDCl3) 4.22 (C(7) --H dd, J 4.5, 9 Hz.), 4.93 (C(6) --H, d, J 4.5 Hz.), 5.5 to 6.1 (C(2) --CH2 and =C--CH2P+, unresolved m), 7.62 (P+CH2CH2CH3, m), 8.55 (P+CH2CH2CH2CH3, m) and 9.1 (P+CH2CH2CH2CH3, d, J 6 Hz.).

Provenance & Evidence