Hydrogen Peroxide → HCID 90224876, compound

HRID 1487094Notes

Reaction equation

HRID 1487094 reaction equation
[NH2:1][C:2]1([C:30]#[N:31])[CH2:7][CH2:6][N:5]([S:8](/[CH:11]=[CH:12]/[C:13]2[C:18]([CH3:19])=[CH:17][C:16]([N:20]3[C:24]([CH3:26])([CH3:25])[C:23](=[O:27])[NH:22][C:21]3=[O:28])=[CH:15][C:14]=2[CH3:29])(=[O:10])=[O:9])[CH2:4][CH2:3]1.[OH-:32].[Na+].OO.[Cl-].[NH4+]>CO.CS(C)=O.CCCCCC.C(OCC)(=O)C>[NH2:1][C:2]1([C:30]([NH2:31])=[O:32])[CH2:7][CH2:6][N:5]([S:8](/[CH:11]=[CH:12]/[C:13]2[C:14]([CH3:29])=[CH:15][C:16]([N:20]3[C:24]([CH3:26])([CH3:25])[C:23](=[O:27])[NH:22][C:21]3=[O:28])=[CH:17][C:18]=2[CH3:19])(=[O:9])=[O:10])[CH2:4][CH2:3]1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 90224811HCID 90224811, compound

Product 1

HCID 90224876HCID 90224876, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-4-amino-1-((4-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-2,6-dimethylstyryl)sulfonyl)piperidine-4-carbonitrile (675 mg, 1.50 mmol) in methanol (7.5 mL) and dimethylsulfoxide (0.195 mL) at room temperature, a 2 N aqueous sodium hydroxide solution (1.6 ml, 1.6 mmol) was added and then a 30% aqueous hydrogen peroxide solution (0.2 mL, 1.95 mmol) were slowly added dropwise. The mixture was stirred at room temperature for one hour. Ethyl acetate, hexane, and a saturated aqueous ammonium chloride solution were added to the reaction mixture. The solid was collected by filtration, washed, and dried to afford (E)-4-amino-1-((4-(5,5-dimethyl-2,4-dioxoimidazolidine-1-yl)-2,6-dimethylstyryl)sulfonyl)piperidine-4-carboxamide (498 mg, 72%).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-7d3a55ed217d40d9abea22d78ece6264
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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