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

HRID 719925Notes

Reaction equation

HRID 719925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][S:23][CH3:24])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[OH:31]O>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][S:23]([CH3:24])=[O:31])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 103223652(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methylsulfanylmethyl-pyrazin-2-yl)-propionamide

Product 1

HCID 100282722(r)-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-n-(5-methanesulfinylmethyl-pyrazin-2-yl)-propionamideYield 51%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4619777ec98c4f6a90c079b8d8e5b98e
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

Loading…