Hexamethyldisilazane → HCID 18626624, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (200 mg, 0.62 mmol) in methylene chloride (2 mL) cooled to 0° C. was treated with N,N-dimethylformamide (2 drops). The reaction mixture was then slowly treated with oxalyl chloride (60 μL, 0.69 mmol). The reaction mixture was stirred at 0° C. for 10 min and then stirred at 25° C. for 1.5 h. The resulting reaction mixture was then treated dropwise with 1,1,1,3,3,3-hexamethyldisilazane (395 μL, 1.87 mmol) and subsequently stirred at 25° C. for 15 h. The reaction mixture was then partitioned between methylene chloride (20 mL), methanol (15 mL), and a 5% aqueous sulfuric acid solution (25 mL). The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/3 hexanes/ethyl acetate) afforded 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (141 mg, 70%) as a white foam: mp 67-70° C. (foam to gel); EI-HRMS m/e calcd for C16H20N2O3S (M+) 320.1195, found 320.1195.

Provenance & Evidence