Diisopropyl Ether → HCID 68671831, compound

Participants

Reaction Steps

To a solution of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propionic acid (200 mg) in dichloromethane (5 mL) was added sequentially a solution of oxalyl chloride in 1 M dichloromethane (0.64 mL) and DMF (16 μL), followed by stirring for 1 hour under ice-cooling. Thereafter, a solution of 5-methylpyridin-2-amine (63 mg) in dichloromethane (5 mL) and pyridine (0.09 mL) were added thereto under ice-cooling, followed by stirring for 2 hours under ice-cooling. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was sequentially washed with a 5% aqueous citric acid solution, saturated aqueous sodium bicarbonate, and saturated brine, and dried over anhydrous magnesium sulfate. The oily substance obtained by concentration was purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1). The obtained oily substance was dissolved in ethyl acetate (4 mL), and 4 M hydrogen chloride/ethyl acetate (1 mL) was added thereto, followed by stirring at room temperature for 30 minutes. The oily substance obtained by concentration was solidified with diisopropyl ether and collected by filtration to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-(5-methylpyridin-2-yl)-3-[(1R)-3-oxocyclopentyl]propanamide monohydrochloride (210 mg) as a white solid.

Provenance & Evidence