Propan-2-one--water (1/1) → HCID 22177238, compound

Participants

Reaction Steps

To a solution of 2-(3′-cyano-biphenyl-4-yl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide (680 mg, 1.6 mmol) in 9 mL of acetone/H2O (2:1 v/v) was added OsO4 (4% in H2O, 100 L, 1 mmol %) and NaIO4 (860 mg, 4.0 mmol, 2.5 eq). The reaction mixture was stirred at r.t. for 6 h. The mixture was then partitioned between CH2Cl2 (20 mL) and 10% NaHCO3 (20 mL) and the organic layer separated. The aqueous layer was extracted with CH2Cl2 (10 mL×3) and the combined organic layer was washed with saturated brine (10 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (20% EtOAc/hexanes) gave 2-(3′-cyano-biphenyl-4-yl)-N-(3,5-dichloro-phenyl)-4-oxobutyramide as a light yellow oil (300 mg, 44%). MS(ESI): 423.0 (M+1).

Provenance & Evidence