Triethylamine → HCID 54294220, compound

Participants

Reaction Conditions

Reaction Steps

Bis(triphenylphosphine) palladium dichloride (120 mg, 0.2 mmol) was added to a deoxygenated mixture of (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(4-[[(trifluoromethyl)sulfonyl)oxy]phenyl]propanoic acid diphenylmethyl ester (3.0 g. 5.2 mmol), t-butyl acrylate (1.5 mL. 10.2 mmol) and triethylamine (4.0 mL. 30.0 mmol) in DMF (50 mL) and the well-stirred suspension was then heated at 90° C. (24 h). The solvent was removed in vacuo and the resulting residue was purified by flash chromatography on silica gel eluting with a mixture of dichloromethane and hexanes (8:1) to give the (S)-2-[[(1,1-dimethylethoxy) carbonyl]amino]-3-(4-[3-(1,1-dimethylethoxy)-3-oxo-1-propenyl]phenyl]propanoic acid diphenylmethyl ester (1.6 g. 2.8 mmol) in 54% yield, mp. 135°-137° C. [α]D -5.35° (0.97% in ethanol).

Provenance & Evidence