Sodium hydride → HCID 22926821, compound

HRID 1985420Notes

Reaction equation

HRID 1985420 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2]1.[H-].[Na+].Br[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26].[Cl-].[NH4+]>CN(C)C=O.O>[C:25]([CH2:24][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([O:17][CH:18]([CH3:19])[CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2]1)([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 22927039HCID 22927039, compound

Product 1

HCID 22926821HCID 22926821, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.75 g of Ethyl 3-(1H-indol-3-yl)-2-isopropoxypropionate was dissolved in 10 ml of N,N-dimethylformamide, and 0.12 g of 60% sodium hydride was added under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes, 0.53 ml of t-butyl bromoacetate was added, and stirring was continued at room temperature for 16 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, and the fraction eluted with 10% ethyl acetate-hexane was evaporated, and the residue was dissolved in 15 ml of dichloromethane. 3 ml of Trifluoroacetic acid was added under ice-cooling, and the mixture was stirred at 0° C. for 7 hours. The reaction solution was diluted with toluene, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (33% ethyl acetate-hexane), to give 0.3 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. waitwas continued at room temperature for 16 hours
  4. temperatureThe reaction solution was cooled with ice
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. washthe fraction eluted with 10% ethyl acetate-hexane
  10. customwas evaporated
  11. dissolutionthe residue was dissolved in 15 ml of dichloromethane
  12. addition3 ml of Trifluoroacetic acid was added under ice-
  13. temperaturecooling
  14. stirringthe mixture was stirred at 0° C. for 7 hours
  15. additionThe reaction solution was diluted with toluene
  16. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f809eb1fa5e7457ba12f3af884b8dcb3
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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