Water → HCID 13606280, compound

HRID 2309244Notes

Reaction equation

HRID 2309244 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH:9]([CH2:13][CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:13][CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH3:28])[C:15]2=[O:23])[C:10]([OH:12])=[O:11])=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13393254HCID 13393254, compound

Product 1

HCID 13606280HCID 13606280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

479 Milligrams of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate prepared in Example 3 and 70 mg of 50% sodium hydride (in oil) were admixed in 5 ml of dimethylformamide, and the mixture was stirred at a room temperature for 1 hour. Then a solution containing 0.23 g of methyl iodide in 3 ml of dimethylformamide was added dropwise gradually to the mixture, and the whole reaction mixture was stirred at a room temperature for 4 hours. The reaction mixture was poured into a large volume of water, and the organic material was extracted with chloroform, then the chloroform layer was washed with water and dried. Chloroform was removed by evaporation to yield 125 mg of 2-(4-chlorobenzoylamino)-3-(1-methyloxindol-3-yl)propionic acid.

Workup

  1. additionwas added dropwise gradually to the mixture
  2. customthe whole reaction mixture
  3. stirringwas stirred at a room temperature for 4 hours
  4. extractionthe organic material was extracted with chloroform
  5. washthe chloroform layer was washed with water
  6. customdried
  7. customChloroform was removed by evaporation

Sources & evidence

ORD record
ord-a6b049a51f414cc1896eb629103a1e0c
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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