tert-Butyl bromoacetate → Benzyl 1-(tert-butoxycarbonylmethyl)-2-indolecarboxylate

HRID 1071692Notes

Reaction equation

HRID 1071692 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][C:25](=[O:28])[CH2:26]Br)([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O>[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:26][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:28])[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 7723355benzyl 1H-indole-2-carboxylate

Product 1

HCID 22612588Benzyl 1-(tert-butoxycarbonylmethyl)-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 18.80 g 1H-indole-2-carboxylic acid benzyl ester in 70 ml N,N-dimethylformamide 1.98 g sodium hydride were added at 0C. After stirring for 1 hour 15.91 ml bromo-acetic acid tert.-butyl ester were added to the mixture and the reaction mixture was stirred for 2 hours at room temperature. After removal of the solvent under reduced pressure the residue was partitioned between 300 ml water and 300 ml dichloromethane. The aqueous layer was washed twice with additional 200 ml dichloromethane. Subsequently the combined organic phases were washed with a saturated aqueous solution of sodium chloride. After filtration the solvent was removed under reduced pressure and the residue was crystallized from ethoxy-ethane/heptane. The product was obtained as a white solid.

Workup

  1. additionwere added to the mixture
  2. customAfter removal of the solvent under reduced pressure the residue
  3. customwas partitioned between 300 ml water and 300 ml dichloromethane
  4. washThe aqueous layer was washed twice with additional 200 ml dichloromethane
  5. washSubsequently the combined organic phases were washed with a saturated aqueous solution of sodium chloride
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customthe residue was crystallized from ethoxy-ethane/heptane
  9. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-b641c98e1e1141ffb2fdbdbd6e14ee59
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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