Sodium Chloride → HCID 20186089, compound

HRID 2309245Notes

Reaction equation

HRID 2309245 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)[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[NH2-].[Na+].[CH2:28](Cl)[CH:29]=[CH2:30].[Cl-].[Na+].CN(C)C=[O:37]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([O:37][CH2:28][CH:29]=[CH2:30])[CH:15]=2)[C:10]([OH:12])=[O:11])=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 7850Allyl chlorideHCID 24533Sodium amideHCID 13393254HCID 13393254, compound

Product 1

HCID 20186089HCID 20186089, compound

Procedure

479 Milligrams of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate prepared in Example 3 and 0.05 g of sodium amide were admixed in 5 ml of dimethylformamide, and the mixture was stirred at a room temperature for 2 hours. Then 0.17 g of allyl chloride was added to the mixture and the resulting reaction mixture was stirred at a room temperature for 10 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 residure thus obtained was purified by means of a silica gel column chromatography to yield 85 mg of 2-(4-chlorobenzoylamino)-3-(1-allyloxyindol-3-yl)propionic acid.

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at a room temperature for 10 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 residure thus obtained
  8. customwas purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-9515d0a1b4914cecab75dcf208c2d7cc
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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