反应详情

温度

0 °C

A mixture of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-[5-(cyano-hydroxy-methyl)-pyrazin-2-yl]-3-cyclopentyl-propionamide (prepared as in Example 26, 100 mg, 0.22 mmol) and potassium carbonate (400 mg, 2.9 mmol) in dimethyl sulfoxide (6 mL) was cooled to 0° C. and then was treated dropwise with a 30% aqueous hydrogen peroxide solution (2 mL). The reaction was stirred at 0° C. for 1 h. The resulting mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water (3×30 mL) and a saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, ethyl acetate) afforded N-[5-(carbamoyl-hydroxy-methyl)-pyrazin-2-yl]-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (30 mg, 28%) as a white solid: (ES)+-HRMS m/e calcd for C21H25ClN4O5S (M+H)+ 481.1314, found 481.1307.

1. customThe resulting mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
4. washThe combined organic layers were washed with water (3×30 mL)
5. dry with materiala saturated aqueous sodium chloride solution (1×30 mL), dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo