Triphenylarsine → HCID 21063260, compound

Participants

Reaction Conditions

Reaction Steps

In a dry 25 ml round bottom flask fitted with a reflux condenser vented through a three way valve attached to a vacuum source and nitrogen gas, 2-bromobenzonitrile (557 mg, 3.06 mmol), tris(dibenzylideneacetone)dipalladium (0), (51 mg, 0.056 mmol), LiCl (353 mg, 8.34 mmol), and AsPh3 (68 mg, 0.22 mmol) were added, followed by 13 ml of N-methylpyrrolidinone. The mixture was degassed and stirred for 10 minutes. A solution of (S)-2-tert-butoxycarbonylamino-3-(4-trimethylstannylphenyl) propionic acid methyl ester (1.23 g, 2.78 mmol) in N-methylpyrrolidinone (4.5 ml) was then added and the reaction was heated at 80° C. for 5 h and left overnight at room temperature. The reaction mixture was diluted with EtOAc (25 ml), quenched by addition of 10 ml of saturated KF solution and stirred for 20 minutes. The reaction mixture was partitioned between water (40 ml) and EtOAc (100 ml). The organic layer was separated, washed with water (6×40 mil and dried (MgSO4). The solvents were removed under reduced pressure and the resulting crude was purified by flash chromatography (9:1 to 7:3 hexanes/EtOAc) to give (S)-2-tert-butoxycarbonylamino-3-(2′-cyano-biphenyl-4-yl) propionic acid methyl ester (570 mg, 54%) as a white solid.

Provenance & Evidence