Benzyl Bromide → HCID 22012989, compound

HRID 1953306Notes

Reaction equation

HRID 1953306 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:28])([O:6][C:7]([CH2:9][C:10]1([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])=[O:8])[CH3:5].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH2:29]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][C:7]([O:6][C:4]([CH3:28])([CH3:3])[CH3:5])=[O:8])([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]1=[O:19])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22013049HCID 22013049, compound

Product 1

HCID 22012989HCID 22012989, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.05 g of sodium hydride (60%) in 5 ml of N,N-dimethylformamide was added dropwise a solution of 0.36 g of 3,3-bis((1,1-dimethylethoxy)carbonylmethyl)indolin-2-one in 5 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After stirring the mixture at that temperature for 30 minutes, 0.12 ml of benzyl bromide was added thereto. The whole mixture was stirred for 1 hour and then concentrated. Chloroform was added to the concentrate, and the mixture was washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 1-benzyl-3,3-bis((1,1-dimethylethoxy)carbonylmethyl)indolin-2-one.

Workup

  1. stirringThe whole mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the concentrate
  4. washthe mixture was washed with an aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-478cef546b3747c688af32e23e2132fa
Source dataset
uspto-grants-2000_09
Patent number
US06114536

Reaction notes

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