Water → HCID 178524821, compound
Reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C@H:15]2[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[OH-].[Li+].O>CO>[OH:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([N:9]2[C:10]([C:11]([F:12])([F:13])[F:14])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:16][CH2:17]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
trans-1-(4-Hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (62.3 mg, 0.203 mmol, prepared in Example 71, Step 1) was dissolved in methanol (0.3 mL). Lithium hydroxide (7.1 mg, 0.297 mmol) and water (0.3 mL) were added and the mixture was heated at 80° C. for 1 hour. After cooling to room temperature, the methanol was removed in vacuo. Tetrahydrofuran was added and removed in vacuo to insure complete removal of methanol. The residue was diluted with water and acidified with 6N HCl. Solid initially precipitated out of solution but quickly went to an oil/gum. The mixture was extracted with methylene chloride two times. The two organic phases were combined, washed with water, dried over sodium sulfate and concentrated to give trans-1-(4-hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (35.8 mg; 63%). Mass spectrum: m/z: 277.1 (M−H).
Workup
- temperatureAfter cooling to room temperature
- customthe methanol was removed in vacuo
- additionTetrahydrofuran was added
- customremoved in vacuo
- customremoval of methanol
- additionThe residue was diluted with water
- customSolid initially precipitated out of solution
- extractionThe mixture was extracted with methylene chloride two times
- washwashed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f9de9af8ffba4ae8847149d413a1b281
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728029B2
Reaction notes
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