Hydrogen Peroxide → HCID 89886887, compound

HRID 1403087Notes

Reaction equation

HRID 1403087 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:16]=[C:15]([C:17]3[C:26]4[C:21](=[C:22](B5OC(C)(C)C(C)(C)O5)[CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][N:18]=3)[CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH2:4][CH2:3]1.[NH:36]1[CH:40]=[C:39]([C:41]2[CH:42]=[N:43][N:44]([CH2:46][CH:47]([CH3:49])[CH3:48])[CH:45]=2)[N:38]=[CH:37]1.[OH-:50].[Na+].OO.[OH2:54]>CO.CS(C)=O.[Cu-]=O.C(O)C.C(Cl)(Cl)Cl>[OH:50][CH:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]2[CH:16]=[C:15]([C:17]3[C:26]4[C:21](=[C:22]([N:36]5[CH:40]=[C:39]([C:41]6[CH:42]=[N:43][N:44]([CH2:46][CH:47]([CH3:49])[CH3:48])[CH:45]=6)[N:38]=[CH:37]5)[CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][N:18]=3)[CH:14]=[CH:13][C:10]=2[C:11]([NH2:12])=[O:54])[CH2:6][CH2:7]1

Participants

11

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 89886791HCID 89886791, compoundHCID 178448442HCID 178448442, compound

Product 1

HCID 89886887HCID 89886887, compoundYield 26%

Reagents, catalysts & solvents 5

HCID 178419072HCID 178419072, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A suspension of compound (2b) (0.188 g), 4-(1H-imidazol-4-yl)-1-isobutyl-1H-pyrazole (0.0837 g), and copper(I) oxide (0.003 g) in MeOH (200 mL) was stirred, open to air, at room temperature for 2 days. Chloroform was added to the reaction solution, which was then filtered using celite. The solvent was distilled off, and the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain a white solid. An aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 30% aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained white solid in DMSO (3 mL) and ethanol (1.5 mL) at room temperature, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, and the deposit was collected by filtration, then washed with water and ether by sprinkling, and then dried under reduced pressure to obtain compound (52) (0.040 g, yield based on 2 steps: 26%) as a pale yellow solid.

Workup

  1. filtrationwas then filtered
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)
  4. customto obtain a white solid
  5. filtrationthe deposit was collected by filtration
  6. washwashed with water and ether by sprinkling
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-273eb0814b8243f6a39fd4be599dba96
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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