Hydrogen Peroxide → HCID 15484980, compound

HRID 2305837Notes

Reaction equation

HRID 2305837 reaction equation
[OH:1][NH:2][C:3](=[O:22])[C:4]([S:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:23]O>CO>[OH:1][NH:2][C:3](=[O:22])[C:4]([S:13]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)=[O:23])([CH3:12])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 9948873HCID 9948873, compound

Product 1

HCID 15484980HCID 15484980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-hydroxy-2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionamide (400 mg, 1.26 mmol) (prepared in Example 1) was dissolved in methanol (100 ml) and 30% H2O2 (10 ml) was added. The reaction mixture was stirred for 48 hours at room temperature at which time it was cooled to 0° C. and quenched with saturated Na2SO3 (20 ml) solution. The reaction mixture became cloudy. It was stirred for 4 hours before it was concentrated in a room temperature water bath, diluted with water, extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentted. The title compound was isolated by silica gel column chromatography, eluting with 75% ethylacetate:hexane. Low melting solid. Yield: 220 mg (52%); MS: 334.1 (M+H)+; 1H NMR (300 Mz, CDCl3): d 1.11 (s, 2H), 1.22 (s, 3H), 3.84 (s, 3H), 7.00-7.61 (m, 9H).

Workup

  1. temperaturewas cooled to 0° C.
  2. customquenched with saturated Na2SO3 (20 ml) solution
  3. stirringIt was stirred for 4 hours before it
  4. concentrationwas concentrated in a room temperature water bath
  5. additiondiluted with water
  6. extractionextracted with CHCl3
  7. washwashed with H2O
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3918adcb20ad47e49b967359dd866e96
Source dataset
uspto-grants-2002_08
Patent number
US06441023B1

Reaction notes

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