Hydrogen Peroxide → N-[5-(carbamoyl-hydroxy-methyl)-pyrazin-2-yl]-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

HRID 719888Notes

Reaction equation

HRID 719888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]([C:24]#[N:25])[OH:23])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(=O)([O-])[O-:33].[K+].[K+].OO>CS(C)=O>[C:24]([CH:22]([OH:23])[C:19]1[N:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C@@H:12]([C:4]2[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:9])=[O:10])=[C:2]([Cl:1])[CH:3]=2)[CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[N:17][CH:18]=1)(=[O:33])[NH2:25]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 99818302(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-[5-(cyano-hydroxy-methyl)-pyrazin-2-yl]-3-cyclopentyl-propionamide

Product 1

HCID 10322924N-[5-(carbamoyl-hydroxy-methyl)-pyrazin-2-yl]-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamideYield 28.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9ebb63c613fd4a9fa3a6604f076d2567
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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