Nitrogen → (S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (50 mg, 0.4 mmol) in water (0.2 mL) was added to a solution of (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid methyl ester (50 mg, 0.1 mmol), and phenylboronic acid (Aldrich, Cat P20009) (21 mg, 0.18 mmol) in 1,4-dioxane (3.0 mL). The reaction was degassed by N2 for 5 min Tetrakis(triphenylphosphine)palladium(0) (8 mg, 0.007 mmol) was added, and the reaction was degassed for another 5 min The reaction vial was sealed and stirred for 5 h. at 80° C. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by Flash chromatography on a silica gel column (EtOAC:Hexanes, 1:3 to 1:1) to give the (S)-methyl 3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoate (30 mg, 70%). Analytical LCMS (M+H-Boc)+: m/z=256.1.

Provenance & Evidence