Dichloromethane → HCID 67483906, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (200 mg, 0.61 mmol) in toluene (4.8 mL) and N,N-dimethylformamide (12 μL) at 25° C. was treated with a 2.0 M solution of oxalyl chloride in methylene chloride (0.36 mL, 0.73 mmol). This solution was stirred at 25° C. for 30 min. At this time, the reaction was cooled to −60° C. and treated dropwise with a 30% aqueous ammonium hydroxide solution (0.59 mL, 5.24 mmol). The resulting suspension was allowed to gradually warm to 25° C. and stirred at 25° C. for 1 h. The reaction mixture was then extracted with ethyl acetate (3×25 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Biotage Flash 40S column, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (175 mg, 88%) as a colorless oil: [α]23589=−45.8° (c=0.096, chloroform); EI-HRMS m/e calcd for C15H20ClNO3S (M+) 329.0852, found 329.0851.

Provenance & Evidence