Sodium Chloride → HCID 20186090, compound

HRID 2309246Notes

Reaction equation

HRID 2309246 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]#[CH:30].[Cl-].[Na+]>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]([CH2:30][C:29]#[CH:28])[C:15]2=[O:23])[C:10]([OH:12])=[O:11])=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 13393254HCID 13393254, compound

Product 1

HCID 20186090HCID 20186090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 2 hours. Then 0.17 g of propargyl chloride was added to the reaction mixture and the whole reaction mixture was stirred at a room temperature for 7 hours. The reaction mixture was poured into 13 ml of a saturated sodium chloride aqueous solution, and the organic material was extracted with chloroform. The chloroform layer was washed with water, dried, then chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography to yield 80 mg of 2-(4-chlorobenzoylamino)-3-[1-(2-propynyl)oxindol-3-yl]propionic acid.

Workup

  1. customthe whole reaction mixture
  2. stirringwas stirred at a room temperature for 7 hours
  3. extractionthe organic material was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. customdried
  6. customchloroform was removed by evaporation
  7. customThe residue thus obtained
  8. customwas purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-eb06fd616151478888a26269221b18c7
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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