Tris(furan-2-yl)phosphane → HCID 131717298, compound

Participants

Reaction Steps

A solution of diphenylmethyl 7-(t-butyloxycarbonylamino)-3-trifluoromethylsulfonyloxy-3-cephem-4-carboxylate (307 mg, 0.50 mmol) and 4-(2-propoxy)-3-(tri-n-butylstannyl)cyclobut-3-ene-1,2-dione (236 mg, 0.55 mmol) in N-methyl-2-pyrrolidinone (NMP, 4.5 mL) was degassed with a gentle stream of argon. Tris(2-furyl)phosphine (11.5 mg, 0.050 mmol), zinc chloride (136 mg, 1.0 mmol), and bis(dibenzylidene-acetone) palladium (0) (14.4 mg, 0.025 mmol) were successively added. The mixture was stirred at an oil bath temperature of 60°-65° C. for 0.5 hr and was diluted with ethyl acetate. The resulting solution was sequentially washed with saturated aqueous NH4Cl (3X), H2O, and saturated NaCl and then was dried over Na2SO4. The filtrate was concentrated, and a solution of the residue in acetonitrile was washed with n-pentane (3X). Removal of the acetonitrile left a dark oil which was chromatographed on SiO2 (19 g) with methylene chloride-acetone (97:3) to afford the title compound (228 mg, 75% yield) as a bright yellow solid. Recrystallization from diisopropyl ether gave the analytical sample.

Provenance & Evidence