Water → HCID 22380638, compound

HRID 895629Notes

Reaction equation

HRID 895629 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:19][CH2:20][CH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22]1=[O:30])[CH2:12][CH2:13]OS(C)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:21]2([C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:30])[CH2:20][CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 22380703HCID 22380703, compound

Product 1

HCID 22380638HCID 22380638, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[2-[N-(Benzyloxycarbonyl)-N-(2-methanesulfonyloxyethyl)amino]ethyl]-2,3-dihydro-1H-indol-2-one (158 mg) was dissolved in N,N-dimethylformamide (3 ml), added with sodium hydride (60%, in oil, 29.2 mg) and stirred at room temperature for 1.5 hours. The reaction mixture was added with water (10 ml) and extracted twice with dichloromethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1) to obtain 74.6 mg of the title compound. Yield: 61%.

Workup

  1. extractionextracted twice with dichloromethane (10 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-42e538cd5d8b48098f179cd915c13d02
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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