1H-Indole-3-propanoic acid → HCID 15675535, compound

HRID 1614195Notes

Reaction equation

HRID 1614195 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:2]1.[C:15]([O:24][CH3:25])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:18].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]([O:24][CH3:25])=[O:23])=[O:14])=[CH:2]1

Participants

5

Reactant 3

HCID 37441H-Indole-3-propanoic acidHCID 8635Methyl AnthranilateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 15675535HCID 15675535, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-indolyl)propionic acid (6.0 g, 32 mmol) in 100 ml THF at room temperature was added 1,1-carbonyldiimidazole (5.14 g, 32 mmol). The reaction mixture was stirred under a dry atmosphere for 30 minutes, after which methyl anthranilate (4.79 g, 32 mmol) was added, and the reaction mixture was stirred at reflux for 30 minutes. No reaction was detected by thin layer chromatography (TLC). Pyridinium p-toluenesulfonate (PPTS) [6.36 g, 25 mmol] was added, and the mixture was stirred at reflux for two days. The reaction mixture was allowed to cool, and the solvent was removed in vacuo. The resulting product was taken up in ethyl acetate and washed (1N HCl, H2O, saturated NaHCO3, and brine) and dried over anhydrous magnesium sulfate. Concentration in vacuo provided a light yellow solid which, when triturated with ethyl acetate/hexane, gave, upon filtration, 7.19 g (70% yield) of 3-(3-indolyl)-N-(2-methoxycarbonylphenyl)propionamide as an off white granular solid.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureat reflux for 30 minutes
  3. stirringthe mixture was stirred
  4. temperatureat reflux for two days
  5. temperatureto cool
  6. customthe solvent was removed in vacuo
  7. washwashed (1N HCl, H2O, saturated NaHCO3, and brine)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationConcentration in vacuo
  10. customprovided a light yellow solid which, when
  11. customtriturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6530a98b59f74cd48dae9576aef7de89
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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