Hydrogen Peroxide → HCID 59278114, compound

HRID 559740Notes

Reaction equation

HRID 559740 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C@@H:9]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:10][CH3:11])[CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-:20].[K+].[K+].OO>CS(C)=O.CCOC(C)=O>[CH3:18][C:15]([S:13]([NH:12][C@H:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:20])[CH:8]=1)[CH2:10][CH3:11])=[O:14])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 59278503HCID 59278503, compound

Product 1

HCID 59278114HCID 59278114, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled (10° C.) rapidly stirred solution of 2-methyl-propane-2-sulfinic acid [(S)-1-(2-cyano-pyridin-4-yl)-propyl]-amide (4.4 g, 16.58 mmol) in DMSO (70 mL) was added potassium carbonate (3 g, 21.72 mmol) portionwise followed by a 30% aqueous solution of hydrogen peroxide (6.16 mL, 54.38 mmol) dropwise. The reaction was stirred at room temperature for 3.5 hours. The reaction was cooled to 5° C., diluted with EtOAc (100 mL), quenched with 10% aqueous sodium thiosulfate solution (25 mL), and stirred for 1 hour. The organic layer was separated, and the aqueous layer was extracted with EtOAc (4×100 mL). The combined organic layers were washed with water (3×50 mL), brine (20 mL), dried over sodium sulfate, filtered and concentrated to afford 4-[(S)-1-(2-methyl-propane-2-sulfinylamino)-propyl]pyridine-2-carboxylic acid amide as a thick colorless oil.

Workup

  1. temperatureThe reaction was cooled to 5° C.
  2. customquenched with 10% aqueous sodium thiosulfate solution (25 mL)
  3. stirringstirred for 1 hour
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (4×100 mL)
  6. washThe combined organic layers were washed with water (3×50 mL), brine (20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-66c8812ab3b7463fb1ee7e54b15d2760
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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