Hydrogen Peroxide → HCID 66817527, compound

HRID 1755111Notes

Reaction equation

HRID 1755111 reaction equation
[OH-].[Na+].OO.[CH2:5]([O:8][CH2:9][CH2:10][N:11]([CH3:35])[C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][S:21]([N:24]2[CH2:29][CH2:28][C:27]([NH2:32])([C:30]#[N:31])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[C:15]([CH3:33])[CH:14]=1)[CH:6]=[CH2:7].S([O-])([O-])=[O:37].[Na+].[Na+]>CO.CS(C)=O>[CH2:5]([O:8][CH2:9][CH2:10][N:11]([CH3:35])[C:12]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][S:21]([N:24]2[CH2:25][CH2:26][C:27]([NH2:32])([C:30]([NH2:31])=[O:37])[CH2:28][CH2:29]2)(=[O:22])=[O:23])=[C:15]([CH3:33])[CH:14]=1)=[O:34])[CH:6]=[CH2:7]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 66818447HCID 66818447, compound

Product 1

HCID 66817527HCID 66817527, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A 1 N aqueous sodium hydroxide solution (1.41 ml) and 30% aqueous hydrogen peroxide (0.95 ml) were added to a solution of the resulting N-(2-allyloxy-ethyl)-4-[2-(4-amino-4-cyano-piperidine-1-sulfonyl)-ethyl]-3,N-dimethyl-benzamide in methanol (24 ml)-DMSO (1.3 ml), and the mixture was stirred at room temperature for one hour. A 10% (w/w) aqueous sodium sulfite solution (2.64 ml) was added to the reaction solution, and the mixture was stirred at room temperature for 40 minutes. The precipitated insoluble matter was then removed by filtration. The resulting filtrate was concentrated under reduced pressure to give 1-(2-{4-[(2-allyloxy-ethyl)-methyl-carbamoyl]-2-methyl-phenyl}-ethanesulfonyl)-4-amino-piperidine-4-carboxylic amide (2.13 g). This was used in the next reaction without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 40 minutes
  2. customThe precipitated insoluble matter was then removed by filtration
  3. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49d4c971f89b4c73918fefe525bd0fb1
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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