Sodium Hydroxide → HCID 19085301, compound

HRID 963036Notes

Reaction equation

HRID 963036 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][CH:40]=[CH:39][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]([CH2:18][CH3:19])=[N:16][N:15]=[C:14]1[CH2:20][NH:21][C:22]([C:24]1[N:25]([CH2:33][C:34]([O:36]CC)=[O:35])[C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[O:5].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:42]=[CH:41][CH:40]=[CH:39][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]([CH2:18][CH3:19])=[N:16][N:15]=[C:14]1[CH2:20][NH:21][C:22]([C:24]1[N:25]([CH2:33][C:34]([OH:36])=[O:35])[C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22439222HCID 22439222, compound

Product 1

HCID 19085301HCID 19085301, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-ethyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate (1.0 g) and a solution of sodium hydroxide (0.13 g) in ethanol were added to ethanol (20 ml), and the mixture was stirred at 50° C. for 1 hour. 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 to give 0.34 g of 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-ethyl[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-98a353edcfa84c9a8e26989a7f9a8638
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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