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-Eintrag

ord-4619777ec98c4f6a90c079b8d8e5b98e

Quelldatensatz

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07132425B2