Sodium Hydroxide → 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylic acid

HRID 1717338Notes

Reaction equation

HRID 1717338 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[N:14]=[N:13]2)=[C:8]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)=[O:5])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[N:14]=[N:13]2)=[C:8]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68515694ethyl 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 685163141-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylic acidYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-{4-[(ethylamino)carbonyl]-2-(3-phenylpropoxy)phenyl}-1H-1,2,3-triazole-4-carboxylate (0.22 g) obtained in Example 133d) in ethanol (6 ml) was added 1N aqueous sodium hydroxide solution (1.0 ml), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the residue was diluted with water. The obtained aqueous solution was washed with ethyl acetate, acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a pale-yellow oil (0.21 g, 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. washThe obtained aqueous solution was washed with ethyl acetate
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f4dddb026e7145cf9e814124a9d0cd9e
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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