Hydrogen Peroxide → 3-[4-(3-Cyclopentyloxy-4-cyclopropylmethoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

HRID 1819342Notes

Reaction equation

HRID 1819342 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:18]3[CH2:22][N:21]([C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[C:26]#[N:27])[C:20](=[O:31])[CH2:19]3)[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:32].[Na+].OO>CCO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:18]3[CH2:22][N:21]([C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[C:26]([NH2:27])=[O:32])[C:20](=[O:31])[CH2:19]3)[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 688278463-[4-(3-Cyclopentyloxy-4-cyclopropylmethoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

Product 1

HCID 688277643-[4-(3-Cyclopentyloxy-4-cyclopropylmethoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

To a dry round bottom flask was added 3-[4-(3-cyclopentyloxy-4-cyclopropylmethoxy-phenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile (1 mmol) in 10 mL EtOH. This mixture was then heated, and 50 μL of 25% NaOH solution followed by 0.5 mL 30% H2O2 was added to the solution. The mixture was stirred at 45 to 50° C. for 4 h, cooled to r.t., and concentrated under reduced pressure. The residue was dissolved in EtOAc (or CH3Cl), washed with saturated NH4Cl, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give pure product. Yield: 87%.

Workup

  1. temperatureThis mixture was then heated
  2. additionwas added to the solution
  3. temperaturecooled to r.t.
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in EtOAc (or CH3Cl)
  6. washwashed with saturated NH4Cl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. customto give pure product

Sources & evidence

ORD record
ord-eac3ad96265745a2ad781d0c231d0198
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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