Sodium Chloride → HCID 22012996, compound

HRID 1953320Notes

Reaction equation

HRID 1953320 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([NH:17][C:18]([CH3:20])=[O:19])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[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>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([NH:17][C:18]([CH3:20])=[O:19])[C:9]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 562745159884-40-9HCID 23665647Potassium tert-butoxide

Product 1

HCID 22012996HCID 22012996, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 0.84 g of (RS)-1-benzyl-3-(methylcarbonylamino)indolin-2-one in 15 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 10 minutes. To the solution was added dropwise 1.11 ml of ethyl bromoacetate, followed by stirring at the same temperature for 30 minutes. The reaction mixture was poured into 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/ethyl acetate=3/1) to give 0.83 g (76%) of the title compound as a colorless oil.

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/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-f08544940d994b2f829f0ed9e8245082
Source dataset
uspto-grants-2000_09
Patent number
US06114536

Reaction notes

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