Hydrogen Peroxide → HCID 66975222, compound

HRID 1022674Notes

Reaction equation

HRID 1022674 reaction equation
[C:1]([CH2:3][CH:4]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1)#[N:2].C(=O)([O-])[OH:27].[Na+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[NH2:2][C:1](=[O:27])[CH2:3][CH:4]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 66975209HCID 66975209, compound

Product 1

HCID 66975222HCID 66975222, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl (6RS,7RS)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (900 mg) in methanol (7 mL)-water (2 mL) were added saturated aqueous sodium hydrogen carbonate (1 mL) and 35% aqueous hydrogen peroxide (3 mL), and the mixture was stirred for 3 days. To the reaction mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (492 mg).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6991a77a0e834333986bd1056e7c0ca6
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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