Water → HCID 22380620, compound

HRID 895627Notes

Reaction equation

HRID 895627 reaction equation
C([N:8]([CH2:12][CH2:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:23])[CH2:9][CH2:10][OH:11])C1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(=O)([O-])O.[K+].O>ClCCl>[CH2:28]([O:27][C:25]([N:8]([CH2:12][CH2:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:23])[CH2:9][CH2:10][OH:11])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516893Potassium BicarbonateHCID 22380725HCID 22380725, compound

Product 1

HCID 22380620HCID 22380620, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[2-[N-Benzyl-N-(2-hydroxyethyl)amino]ethyl]-2,3-dihydro-1H-indol-2-one (463 mg) was dissolved in dichloromethane (9.2 ml), added with benzyl chloroformate (0.51 ml) and potassium hydrogencarbonate (358 mg) and stirred at room temperature for 24 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 dissolved in methanol (10 ml), added with 1 N aqueous sodium hydroxide (2.2 ml) and stirred for 30 minutes. The reaction mixture was added with water (50 ml) and extracted twice with dichloromethane (40 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: ethyl acetate) to obtain 272 mg of the title compound. Yield: 52%.

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. dissolutionThe residue was dissolved in methanol (10 ml)
  5. additionadded with 1 N aqueous sodium hydroxide (2.2 ml)
  6. stirringstirred for 30 minutes
  7. additionThe reaction mixture was added with water (50 ml)
  8. extractionextracted twice with dichloromethane (40 ml)
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-d3943c48488346eab443cb2fe740f104
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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