4-Chlorobenzoic Acid → HCID 13393254, compound

HRID 2309239Notes

Reaction equation

HRID 2309239 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].[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([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:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Product 1

HCID 13393254HCID 13393254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.25 Grams of 2-amino-3-(oxindol-3-yl)propionic acid hydrochloride prepared in reference example 1, and 1.3 g of N-hydroxysuccinimide ester of p-chlorobenzoic acid were dissolved in 50 ml of dimethylformamide. To this solution was added 1.2 g of triethylamine, and the whole mixture was stirred at a room temperature for 3 hours. Dimethylformamide was removed by evaporation, then water was added to the resultant residue, the crystals formed were collected by filtration to obtain 0.68 g of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate. Melting point: 133°-135° C. (decomp.) [α]D25 -50.3° (C=1, methanol)

Workup

  1. customDimethylformamide was removed by evaporation
  2. additionwater was added to the resultant residue
  3. customthe crystals formed
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8dba9e309177443f89e563e8bf897144
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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