Sodium Hydroxide → HCID 19085308, compound

HRID 963038Notes

Reaction equation

HRID 963038 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][CH:44]=[CH:43][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:16][N:15]=[C:14]1[CH2:24][NH:25][C:26]([C:28]1[N:29]([CH2:37][C:38]([O:40]CC)=[O:39])[C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:5].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:46]=[CH:45][CH:44]=[CH:43][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[N:13]1[C:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[N:16][N:15]=[C:14]1[CH2:24][NH:25][C:26]([C:28]1[N:29]([CH2:37][C:38]([OH:40])=[O:39])[C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22439241HCID 22439241, compound

Product 1

HCID 19085308HCID 19085308, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-cyclohexyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate (0.8 g) and a solution of sodium hydroxide (0.08 g) in ethanol was added to ethanol (10 ml), and the mixture was stirred at 50° C. for 30 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 and the extract was dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate-hexane to give 0.36 g of 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-cyclohexyl[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-hexane

Sources & evidence

ORD record
ord-d7c71004401c472581b431821a92d761
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

Loading…