Sodium Hydroxide → 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid
Reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25]CC)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
A solution of the compound (3.96 g, 10.22 mmol) obtained in step 5 and 1N aqueous sodium hydroxide solution (15.33 mL, 15.33 mmol) in ethanol (50 mL) was stirred at room temperature for 2 hr. To the reaction mixture was further added 1N aqueous sodium hydroxide solution (5.0 mL, 5.0 mmol), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. 1N Hydrochloric acid was added thereto, and the precipitate was collected by filtration, and crystallized from ethyl acetate and hexane to give 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid (2.52 g, 7.01 mmol, 69%) as a pale-yellow powder.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure, and water
- additionwas added to the residue
- addition1N Hydrochloric acid was added
- filtrationthe precipitate was collected by filtration
- customcrystallized from ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-671b703e31404410880b8625a0a09735
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156837B2
Reaction notes
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