Sodium Chloride → HCID 13393254, compound

HRID 2309242Notes

Reaction equation

HRID 2309242 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.Cl.[NH2:20][CH:21]([CH2:25][CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][C:27]1=[O:35])[C:22]([OH:24])=[O:23].[Cl-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:20][CH:21]([CH2:25][CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]2=[O:35])[C:22]([OH:24])=[O:23])=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 63184-Chlorobenzoic AcidHCID 62365Isobutyl chloroformateHCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Product 1

HCID 13393254HCID 13393254, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4.84 g of p-chlorobenzoic acid and 4 ml of triethylamine with 50 ml of dimethylformamide, was added dropwise a solution of 3.87 g of isobutyl chloroformate with 2 ml of dimethylformamide, the reaction mixture was stirred at a room temperature for 30 minutes. To the reaction mixture was added dropwise a solution of 5.72 g of 2-amino-3-(oxindol-3-yl)propionic acid hydrochloride prepared in reference example 1 with 3 ml of dimethylformamide, then the whole reaction mixture was stirred at at a room temperature for 30 minutes, next was stirred at 50°-60° C. for 1 hour. After the reaction was completed, the reaction mixture was poured into a large amount of a saturated sodium chloride aqueous solution, and extracted with chloroform. The chloroform layer was washed with water, and dried. The solvent was removed by evaporation to obtain crude crystals, then recrystallized from methanol-water to obtain 3.4 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. customthe whole reaction mixture
  2. stirringwas stirred at at a room temperature for 30 minutes
  3. stirringnext was stirred at 50°-60° C. for 1 hour
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. customdried
  7. customThe solvent was removed by evaporation
  8. customto obtain crude crystals
  9. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-00e8f9908c024f10911f081a062a88a1
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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