Hydrogen Peroxide → HCID 178482533, compound

HRID 493719Notes

Reaction equation

HRID 493719 reaction equation
[C:1](/[CH:3]=[C:4]1/[N:5]([CH3:24])/[C:6](=[N:22]/[CH3:23])/[S:7][CH:8]/1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:2].C(=O)([O-])[O-:26].[K+].[K+].OO>CS(C)=O.C(OCC)(=O)C>[C:1]([CH2:3][C:4]1[N:5]([CH3:24])/[C:6](=[N:22]/[CH3:23])/[S:7][C:8]=1[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:13][CH2:14]1)(=[O:26])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 178482532HCID 178482532, compound

Product 1

HCID 178482533HCID 178482533, compoundYield 120%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-((2Z,4E)-4-(cyanomethylene)-3-methyl-2-(methylimino)-1,3-thiazolidin-5-yl)piperidine-1-carboxylate (0.30 g) obtained in Example 74a) in DMSO (6.0 mL) were added potassium carbonate (0.1 g) and a 30% aqueous hydrogen peroxide solution (1 mL) at 0° C. and mixed for 30 minutes. The reaction solution was diluted with ethyl acetate, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from hexane to give the title compound (0.32 g) as a colorless solid.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off
  4. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-ac8f7ee8b91f40a6a2f3f7a409e01bef
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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