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Sodium Hydroxide → 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoic acid

HRID 1750432
Notes
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Reaction equation

HRID 1750432 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]([CH:22]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[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.C1COCC1.O.Cl>[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]([CH:22]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]([OH:25])=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 86721274ethyl 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoate

Product 1

HCID 867212752-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoic acidYield 87%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolvent
HCID 702
Ethanol
Solvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixed solution of the compound (14 mg, 0.03 mmol) obtained in step 1 in ethanol (1.0 mL) and THF (1.0 mL) was added 1N aqueous sodium hydroxide solution (0.059 mL, 0.06 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 hr. The reaction mixture was diluted with water, 1N hydrochloric acid was added until the mixture became pH 2-3, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure to give 2-(2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)-3-phenylpropanoic acid (11.4 mg, 0.025 mmol, 87%) as a colorless oil.

Workup

  1. additionwas added until the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-afdc700198664071a78b89fc81addd99
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156837B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes