Dimethylformamide → HCID 59331615, compound

Participants

Reaction Steps

To a solution (15 mL) of 3-cyclopentyl-2-[4-(methylsulfonyl)phenyl]propanoic acid (5.00 g) in dichloromethane were added oxalyl chloride (7.30 mL) and a catalytic amount of N,N-dimethylformamide under ice-cooling and the mixture was stirred for 30 min. The reaction mixture was concentrated, and the residue was dissolved in tetrahydrofuran (15 mL). Thereto was added triethylamine (9.4% mL) at room temperature, and the mixture was stirred for 30 min. The resulting precipitate was filtered off, enolate separately prepared from acetone (1.08 g) and potassium hydride (2.71 g: 30% wt) in tetrahydrofuran (15 mL) was added to the filtrate at −78° C., and the mixture was stirred for 1 hr. is The reaction mixture was slowly warmed to room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, 1N hydrochloric acid was added and the mixture was stirred for 30 min. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative high performance liquid chromatography, and the title compound (1.60 g, yield 28%) was obtained as colorless amorphous crystals. MS: 337 (MH+).

Provenance & Evidence