Hydrogen Peroxide → tert-butyl (6R,7R)-6-(2-amino-2-oxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022670Notes

Reaction equation

HRID 1022670 reaction equation
[C:1]([CH2:3][C@H:4]1[C@H: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-])[O-:27].[K+].[K+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[NH2:2][C:1](=[O:27])[CH2:3][C@H:4]1[C@H: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

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 66975920tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976771tert-butyl (6R,7R)-6-(2-amino-2-oxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylateYield 71.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl (6R,7R)-6-(cyanomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1 g) in DMSO (10 mL) were added potassium carbonate (0.502 g) and 30% aqueous hydrogen peroxide (1.22 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hr. Diluted aqueous sodium thiosulfate solution was added, 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 to give the title compound (746 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

Sources & evidence

ORD record
ord-d13f28fec89745bda92720aa04f557aa
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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