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Hydrochloric Acid → 2-{4-[(9R)-9-Hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionic acid

HRID 579388
Notes
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Reaction equation

HRID 579388 reaction equation
[OH:1][C@@:2]1([C:35]([F:38])([F:37])[F:36])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[CH:11]=[C:10]([C:22]3[CH:23]=[N:24][N:25]([C:27]([CH3:34])([CH3:33])[C:28]([O:30]CC)=[O:29])[CH:26]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[Na+].Cl>C(O)C>[OH:1][C@@:2]1([C:35]([F:37])([F:38])[F:36])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:19])[CH3:20])[CH:11]=[C:10]([C:22]3[CH:23]=[N:24][N:25]([C:27]([CH3:33])([CH3:34])[C:28]([OH:30])=[O:29])[CH:26]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117599404Ethyl 2-{4-[(9R)-9-hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionate

Product 1

HCID 1175992732-{4-[(9R)-9-Hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionic acidYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-{4-[(9R)-9-hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionate (68.4 g) was dissolved in ethanol (256 ml), 4N aqueous sodium hydroxide (128 ml) was added, and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was ice-cooled, 2N hydrochloric acid (333 ml) was added dropwise, and the mixture was extracted with ethyl acetate (500 ml). The obtained organic layer was washed successively with water (400 ml, twice) and saturated brine (400 ml). The obtained organic layer was dried over anhydrous sodium sulfate, the insoluble material was filtered off, and the solvent in the filtrate was evaporated to give the title compound (70.0 g).

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate (500 ml)
  3. washThe obtained organic layer was washed successively with water (400 ml
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationthe insoluble material was filtered off
  6. customthe solvent in the filtrate was evaporated

Sources & evidence

ORD record
ord-592beed285b84ce1aea36cbe40250baf
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040717B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes