Sodium Chloride → HCID 22012986, compound

HRID 378710Notes

Reaction equation

HRID 378710 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C:7]([NH:9][CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])=[O:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].[Cl-].[Na+]>CS(C)=O>[CH2:33]([O:32][C:30]([CH2:29][C:10]1([NH:9][C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:21][CH:20]=2)=[O:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]1=[O:19])=[O:31])[CH3:34]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 22012981HCID 22012981, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22012986HCID 22012986, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 0.72 g of (RS)-3-((4-methylbenzyl)carbonylamino)indolin-2-one in 20 ml of dry dimethyl sulfoxide was added 3 ml of a 1M solution of potassium t-butoxide in dry dimethyl sulfoxide at room temperature under a nitrogen atmosphere, followed by stirring for 30 minutes. To the mixture was added dropwise 0.37 ml of ethyl bromoacetate, followed by stirring at the same temperature for 30 minutes. The reaction mixture was treated with an aqueous solution of sodium chloride and extracted with ethyl ether. The ethyl ether layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=40/1) to give 0.30 g (32%) of the title compound.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. extractionextracted with ethyl ether
  3. dry with materialThe ethyl ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-8559c3c3415b4fa5a769b52a51cb6773
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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