Water → HCID 20186091, compound

HRID 2309247Notes

Reaction equation

HRID 2309247 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+].[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.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]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:15]2=[O:23])[C:10]([OH:12])=[O:11])=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 13393254HCID 13393254, compound

Product 1

HCID 20186091HCID 20186091, 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 mixture containing of 0.17 ml of benzyl chloride in 3 ml of dimethylformamide was added dropwise slowly into the reaction 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 dried and chloroform was removed by evaporation. There was obtained 110 mg of 2-(4-chlorobenzoylamino)-3-(1-benzyloxindol-3-yl)propionic acid.

Workup

  1. additionwas added dropwise slowly into the reaction 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. dry with materialthe chloroform layer was dried
  6. customchloroform was removed by evaporation

Sources & evidence

ORD record
ord-a271cceda171437492868fae172aeaa6
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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