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

HRID 963026Notes

Reaction equation

HRID 963026 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[CH:17]=[N:16][N:15]=[C:14]1[CH2:18][NH:19][C:20]([C:22]1[N:23]([CH2:31][C:32]([O:34]CC)=[O:33])[C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[O:5].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:40]=[CH:39][CH:38]=[CH:37][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[CH:17]=[N:16][N:15]=[C:14]1[CH2:18][NH:19][C:20]([C:22]1[N:23]([CH2:31][C:32]([OH:34])=[O:33])[C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67727845HCID 67727845, compound

Product 1

HCID 677277702-(4-(3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetic acidYield 23.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate (2.0 g) and a solution of sodium hydroxide (0.39 g) in ethanol were added to ethanol (20 ml), and the mixture was stirred at 50° C. for 20 minutes. The solvent was evaporated, and the residue was dissolved in water. Toluene was added to the solution for washing. The aqueous layer was taken out, and 2M hydrochloric acid was added to adjust the solution to pH 2. The solution was extracted with chloroform. The extract was dried over magnesium sulfate, and the solvent was evaporated. The residue was recrystallized from ethyl acetate to give 0.45 g of 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetic acid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. additionToluene was added to the solution
  4. washfor washing
  5. addition2M hydrochloric acid was added
  6. extractionThe solution was extracted with chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-046e7d5dd3f54c808c2b7bbec9a17cac
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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