Ethyl Acetate → HCID 69073585, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 3-{6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}-2-(diethoxyphosphoryl)propanoate (1.058 g, 2.31 mmol) in dry THF (4 mL) was added to a solution of sodium hydride (0.111 g, 60% in mineral oil, 2.77 mmol) in dry TBF (3 mL) at 0° C. and the mixture was stirred at 0° C. for 60 min. To this mixture a solution of 3-(1,1′-biphenyl-3-yl)propanal (0.582 g, 2.77 mmol) in dry TBF (3 mL) was added, and the reaction mixture was allowed to attain room temperature over 22 h. EtOAc was then added, and the organic phase was washed with saturated aqueous NH4Cl and water, dried (Na2SO4) and concentrated. Flash chromatography (toluene/EtOAc, 15:1) of the residue gave tert-butyl 5-(1,1′-biphenyl-3-yl)-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)pent-2-enoate (1.105 g, 93%) as a mixture of E/Z-isomers.

Provenance & Evidence