Hydrogen Peroxide → HCID 70345972, compound

HRID 1738911Notes

Reaction equation

HRID 1738911 reaction equation
OO.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[C:12](=[O:24])[C@@H:11]([CH2:25][C:26]#[N:27])[O:10][C@H:9]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)[C:8]=2[CH:38]=1.C(=O)([O-])[O-:40].[K+].[K+]>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[C:12](=[O:24])[C@@H:11]([CH2:25][C:26]([NH2:27])=[O:40])[O:10][C@H:9]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)[C:8]=2[CH:38]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 70345096HCID 70345096, compound

Product 1

HCID 70345972HCID 70345972, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrogen peroxide solution (30% w /v in H2O, 4 ml) was added to a suspension of trans-7-chloro-5-(1-naphthyl)-1-(4-(2-methylimidazol-1-yl)butyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetonitrile (250 mg, 0.5 mmol) and potassium carbonate (69 mg, 0.5 mmol) in ethanol (10 ml). The mixture was heated at 60° C. for 18 hours. The solvent was removed under reduced pressure, the resulting residue dissolved in dichloromethane and washed with brine. The organic layer was dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash column chromatography (dichloromethane/methanol/ammonia solution 97:3:1) to give a colorless oil. The oil was triturated with hot ethyl acetate/diethyl ether/hexane to give the title compound (98 mg, 38%)as a colorless solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue dissolved in dichloromethane
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (dichloromethane/methanol/ammonia solution 97:3:1)
  7. customto give a colorless oil
  8. customThe oil was triturated with hot ethyl acetate/diethyl ether/hexane

Sources & evidence

ORD record
ord-3a652d8cf51049e08f5e4d7d47f1e031
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

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