Ethanol → HCID 131710572, compound

Participants

Reaction Steps

A solution of t-butyl 3-bromomethyl-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (5.0 g., ca. 10.56 mmole.) in ethyl acetate (90 ml.) was treated with a solution of ethoxycarbonylmethylenetriphenylphosphorane (9.18 g, 26.4 mmole) in ehtyl acetate (110 ml.) and the mixture stirred at 27° for 22 hours, in the dark. The mixture was cooled to ca 3° and stirred for 2 hours after which time precipitated material was collected by filtration and treated as described in Example 1c to give the ylid (3.85 g, 49%) as photosensitive white prisms (from ethyl acetate), m.p. (darkening at ca 155°) ca 178° (decomp.), [α]D27 + 61.5° (C 1.6, CHCl3), λmax. (EtOH) 266 nm. (ε 10,360) and 272 nm. (ε 10,000); the infrared and p.m.r. spectra resembled those of material described above in Example 1c.

Provenance & Evidence