Sodium Chloride → HCID 22013036, compound

HRID 378718Notes

Reaction equation

HRID 378718 reaction equation
[CH2:1]([O:3][CH:4]([O:27][CH2:28][CH3:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[O:17])[C:7]1=[O:26])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[Cl-].[Na+]>CS(C)=O>[CH2:41]([O:40][C:38]([CH2:37][C:8]1([NH:15][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[O:17])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:27][CH2:28][CH3:29])[C:7]1=[O:26])=[O:39])[CH3:42]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 11014797HCID 11014797, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22013036HCID 22013036, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a solution of 7.50 g of (RS)-1-(2,2-diethoxyethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one in 100 ml of dry dimethyl sulfoxide was added 20 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 a solution of 2.30 ml of ethyl bromoacetate in 20 ml of dry dimethyl sulfoxide, followed by stirring at the same temperature for 30 minutes. A sodium chloride aqueous solution was added thereto, and the mixture was 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 (hexane/ethyl acetate=3/1) to afford 8.21 g (90%) of the title compound.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. extractionthe mixture was extracted 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 (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7b86f5d2cba546f4b1bdf5a7f2da76f4
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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