Hydrogen Peroxide → HCID 58305754, compound

HRID 2362232Notes

Reaction equation

HRID 2362232 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]2[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:5]([CH3:31])[CH:4]=1)#[N:2].C(=O)([O-])[O-:33].[K+].[K+].OO.O>CS(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[CH:12][CH:11]=[C:10]2[CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:5]([CH3:31])[CH:4]=1)(=[O:33])[NH2:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 58305762HCID 58305762, compound

Product 1

HCID 58305754HCID 58305754, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred suspension of ethyl 3-(1-(4-cyano-2-methylphenyl)-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-2-yl)propanoate (28B) (120 mg, 0.28 mmol) and potassium carbonate in DMSO (0.2 mL) was added dropwise 30% H2O2 at 0° C. The mixture was allowed to warm to room temperature and stirred 3 h. After water (2 mL) was added, some precipitate appeared, which was separated by centrifuge, rinsed with water (0.5 mL) and dried in vacuum to afford ethyl 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-2-yl)propanoate (28C) as a white solid (100 mg, 80%).

Workup

  1. customwhich was separated by centrifuge
  2. washrinsed with water (0.5 mL)
  3. customdried in vacuum

Sources & evidence

ORD record
ord-7abbcc18b9c24862b18bc0ef934bf367
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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