Hydrogen Peroxide → 2(r)-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-n-(5-methanesulfinylmethyl-pyrazin-2-yl)-propionamide

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methylsulfanylmethyl-pyrazin-2-yl)-propionamide (prepared as in Example 36, 514.3 mg, 1.099 mmol) in formic acid (11 mL) was treated with a 30% aqueous hydrogen peroxide solution (113 μL, 1.106 mmol). The reaction was stirred at 25° C. for 4 d. The reaction was then partitioned between ethyl acetate (250 mL) and water (250 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (250 mL) and a saturated aqueous sodium chloride solution (150 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 5% methanol/methylene chloride) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methanesulfinylmethyl-pyrazin-2-yl)-propionamide (269.9 mg, 51%) as a light yellow foam: mp 102–106° C. (foam to gel); (ES)+-HRMS m/e calcd for C21H26ClN3O4S2 (M+H)+ 484.1126, found 484.1134.

1. customThe reaction was then partitioned between ethyl acetate (250 mL) and water (250 mL)
2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (250 mL)
3. dry with materiala saturated aqueous sodium chloride solution (150 mL), dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD 기록

ord-4619777ec98c4f6a90c079b8d8e5b98e

출처 데이터셋

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07132425B2