4-Chlorobenzoic Acid → HCID 13393254, compound

HRID 2309241Notes

Reaction equation

HRID 2309241 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17])[C:4]([OH:6])=[O:5].P(Cl)(OCC)(OCC)=O.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.C(N(CC)CC)C>[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:2][CH:3]([CH2:7][CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[C:4]([OH:6])=[O:5])=[O:33])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 13139Diethyl chlorophosphateHCID 516892Sodium BicarbonateHCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Product 1

HCID 13393254HCID 13393254, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

1.14 Grams of 2-amino-3-(Oxindol-3-yl)propionic acid hydrochloride prepared in reference example 1, and 0.8 ml of triethylamine were suspended in 10 ml of tetrahydrofuran, then under stirring condition at a room temperature, a solution of 1.0 g of diethyl chlorophosphate with 10 ml of tetrahydrofuran was added dropwise thereto, and the reaction mixture was stirred at a room temperature for 3 hours. A solution of 1.0 g of p-chlorobenzoic acid with 10 ml of tetrahydrofuran was added dropwise to the reaction mixture, and the whole reaction mixture was stirred at a room temperature for additional 10 hours. After the reaction was completed, the crystals formed were removed by filtration, and the filtrate was concentrated, to the residue thus obtained was poured a saturated sodium bicarbonate aqueous solution, then the mixture was extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride aqueous solution, then the chloroform layer was dried with anhydrous sodium sulfate, and the solvent was removed by evaporation. The thus obtained residue was recrystallized from methanol-water to obtain 0.75 g of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate in the form of colorless powdery substance. Melting point: 133°-135° C. (decomp.) [α]D25 -50.3° (C=1, methanol)

Workup

  1. stirringthe reaction mixture was stirred at a room temperature for 3 hours
  2. customthe whole reaction mixture
  3. stirringwas stirred at a room temperature for additional 10 hours
  4. customthe crystals formed
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated, to the residue
  7. customthus obtained
  8. extractionthe mixture was extracted with chloroform
  9. washThe organic layer was washed with water
  10. dry with materiala saturated sodium chloride aqueous solution, then the chloroform layer was dried with anhydrous sodium sulfate
  11. customthe solvent was removed by evaporation
  12. customThe thus obtained residue was recrystallized from methanol-water

Sources & evidence

ORD record
ord-f911b0cfb69d45fbb8069e43cb5f0ac6
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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