HCID 10366670, compound → HCID 10096248, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methylsulfanyl-pyrazin-2-yl)-propionamide (prepared as in Example 4, 0.20 g, 0.441 mmol) in tetrahydrofuran (3 mL) was added dropwise to a solution of sodium-meta-periodate (0.189 g, 0.882 mmol) in water (1.5 mL). The resulting reaction mixture was stirred at 25° C. for 72 h. The reaction mixture was then concentrated in vacuo, and the residue was then diluted with chloroform (25 mL). The organic layer was washed with water (25 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methane-sulfinyl-pyrazin-2-yl)-propionamide (96 mg, 46%) as a white foam: mp 88–95° C. (foam to gel); (ES)+-HRMS m/e calcd for C20H24ClN3O4S2 (M+H)+ 470.0970 found 470.0976.

Provenance & Evidence