Acetic Acid → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylamino)-pyrazin-2-yl]-propionamide

Participants

Reaction Steps

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-triethylsilanyloxy-ethylamino)-pyrazin-2-yl]-propionamide (100 mg, 0.17 mmol) in tetrahydrofuran (2 mL), water (0.5 mL), and acetic acid (2 mL) was stirred at 25° C. for 6 h. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 2/3 hexanes/ethyl acetate to 100% ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylamino)-pyrazin-2-yl]-propionamide (69 mg, 86%) as a white foam: (ES)+-HRMS m/e calcd for C21H27ClN4O4S (M+H)+ 467.1515, found 467.1517.

Provenance & Evidence