Tetrahydrofuran → Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

286 mg (0.75 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptan-2-carboxylate were dissolved in 12 ml of THF under argon and treated with 271 mg (0.75 mmol) of (1-ethoxycarbonylethylidene)-triphenylphosphorane. The yellow solution was stirred at 70° C. for 6 hours and subsequently concentrated. The residue remaining behind was chromatographed over silica gel (0.040-0.063 mm particle size) with ethyl acetate:hexane (9:16) as the eluent.

Provenance & Evidence