Sodium Hydroxide → 2-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetic acid

HRID 963030Notes

Reaction equation

HRID 963030 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:43]=[CH:42][CH:41]=[CH:40][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23]([C:25]1[N:26]([CH2:34][C:35]([O:37]CC)=[O:36])[C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:7]>CO>[Cl:3][C:4]1[CH:43]=[CH:42][CH:41]=[CH:40][C:5]=1[C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][C:9]=1[N:15]1[C:19]([CH3:20])=[N:18][N:17]=[C:16]1[CH2:21][NH:22][C:23]([C:25]1[N:26]([CH2:34][C:35]([OH:37])=[O:36])[C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22439194Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate

Product 1

HCID 190851972-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetic acidYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methanol (60 ml) and a 2M aqueous sodium hydroxide solution (7.0 ml) were added to ethyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate (4.0 g), and the mixture was stirred at 50° C. for 30 minutes and at room temperature for 4 hours. Methanol was evaporated, and water and ethyl acetate were added. The aqueous layer was taken out, and citric acid was added to adjust the solution to pH 3. The solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate to give 2.6 g of 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetic acid.

Workup

  1. customMethanol was evaporated
  2. additionwater and ethyl acetate were added
  3. additioncitric acid was added
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7ae798dabff24b438fcdbdc48628c35d
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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