Sodium Hydroxide → 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrazole-5-carboxylic acid
Reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]([C:18](=[O:29])[CH2:19][N:20]3[N:24]=[N:23][C:22]([C:25]([F:28])([F:27])[F:26])=[N:21]3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([C:18](=[O:29])[CH2:19][N:20]3[N:24]=[N:23][C:22]([C:25]([F:26])([F:28])[F:27])=[N:21]3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
300 mg (0.58 mmol) of ethyl 1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]acetyl}-1H-pyrazole-5-carboxylate were dissolved in 4 ml of ethanol, 282 mg (3.15 mmol) of 2N aqueous sodium hydroxide solution were added and the mixture was stirred at RT for 5 d. The solvent was distilled off under reduced pressure, the residue was taken up in water and the mixture was extracted once with methyl tert-butyl ether. The aqueous phase was then acidified with 2N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated.
Workup
- distillationThe solvent was distilled off under reduced pressure
- extractionthe mixture was extracted once with methyl tert-butyl ether
- extractionextracted three times with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-85f188666f124cb18b2ef928357c310f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791139B2
Reaction notes
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