Ethyl Acetate → HCID 68466697, compound

HRID 503000Notes

Reaction equation

HRID 503000 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]3([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][CH2:11][CH2:10]3)=[N:7][N:6]=[C:5]2[C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23]C)=[O:22])[CH2:3][CH2:2]1.[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1>[CH:1]1([N:4]2[C:8]([C:9]3([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[CH2:10][CH2:11][CH2:12]3)=[N:7][N:6]=[C:5]2[C:18]2[CH:19]=[C:20]([C:21]([OH:23])=[O:22])[CH:25]=[CH:26][CH:27]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 68466949HCID 68466949, compound

Product 1

HCID 68466697HCID 68466697, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-{4-cyclopropyl-5-[1-(2-thienyl)cyclobutyl]-4H-1,2,4-triazol-3-yl}benzoate (206 mg) was dissolved in dioxane (4 ml) and a 1M aqueous sodium hydroxide solution (1.1 ml) was added thereto at room temperature, followed by stirring at the same temperature for 12 hours. The solvent was removed by evaporation and pH was adjusted to 4 by adding an aqueous citric acid solution, followed by extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure to obtain an amorphous. Furthermore, ethyl acetate was added thereto and the whole was heated under stirring to obtain 155 mg of 3-{4-cyclopropyl-5-[1-(2-thienyl)cyclobutyl]-4H-1,2,4-triazol-3-yl}benzenecarboxylic acid (white crystals).

Workup

  1. customat room temperature
  2. customThe solvent was removed by evaporation and pH
  3. additionby adding an aqueous citric acid solution
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customto obtain an amorphous
  9. temperaturethe whole was heated
  10. stirringunder stirring

Sources & evidence

ORD record
ord-d0d528b2d419479b82443b5788802d45
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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