Hydrogen Peroxide → HCID 66975405, compound

HRID 1022724Notes

Reaction equation

HRID 1022724 reaction equation
OO.[C:3]([C:5]1[C:6]([O:11][CH:12]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]2)=[N:7][CH:8]=[CH:9][CH:10]=1)#[N:4].C(=O)([O-])[O-:35].[K+].[K+].O>CS(C)=O>[C:3]([C:5]1[C:6]([O:11][CH:12]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]2)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:35])[NH2:4]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 66975376HCID 66975376, compound

Product 1

HCID 66975405HCID 66975405, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

33% Aqueous hydrogen peroxide (1 mL) was added to a solution of tert-butyl (6RS,7SR)-6-[(3-cyanopyridin-2-yl)oxy]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (100 mg) and potassium carbonate (45 mg) in DMSO (3 mL), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and HPLC to give the title compound (57 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography and HPLC

Sources & evidence

ORD record
ord-b9d9ea679cf04688843ca2b588b5d1fc
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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