Water → HCID 14167864, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of diphenylmethyl 7-phenylacetamido-3-[(benzothiazol-2-yl)thio]-3-cephem-4-carboxylate (IIc, 0.0973 g, 0.00015 mole), bis(dibenzylidene acetone)palladium (0.0044 g, 0.00000765 mole), tri(2-furyl)phosphine (0.006 g, 0.000026 mole), zinc chloride (0.042 g, 0.003 mole) and vinyl tributyl stannane (0.055 mL, 0.00018 mole) in dry tetrahydrofuran (3 mL) was heated under argon atmosphere at 65° C. for 18 h. After that period HPLC indicated no further conversion of compound IIc. Water and ethyl acetate was added to the reaction mixture, and the two phases were separated. The organic phase was separated, dried and concentrated. The crude product obtained was dissolved in acetonitrile and the acetonitrile solution was washed three times with equal volumes of pentane. Flash chromatography (5% dichloromethane in ethyl acetate) recovered starting compound IIc (0.041 g, 42%) and afforded product IIIa (0.0133 g, 17%, 29% when corrected for recovered starting material) as a yellow foam. Recrystallization from ethanol gave the analytical sample.

Provenance & Evidence