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

HRID 579395Notes

Reaction equation

HRID 579395 reaction equation
[OH:1][C@@:2]1([C:36]([F:39])([F:38])[F:37])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])[CH:11]=[C:10]([C:23]3[CH:24]=[N:25][N:26]([C:28]([CH3:35])([CH3:34])[C:29]([O:31]CC)=[O:30])[CH:27]=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:36]([F:38])([F:39])[F:37])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])[CH:11]=[C:10]([C:23]3[CH:24]=[N:25][N:26]([C:28]([CH3:34])([CH3:35])[C:29]([OH:31])=[O:30])[CH:27]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117599138Ethyl 2-{4-[(9R)-9-hydroxy-2-(4-hydroxy-4-methylpentyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionate

Product 1

HCID 1175991392-{4-[(9R)-9-Hydroxy-2-(4-hydroxy-4-methylpentyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-{4-[(9R)-9-hydroxy-2-(4-hydroxy-4-methylpentyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionate (218 mg) was dissolved in ethanol (2.2 ml), 4N aqueous sodium hydroxide (320 μl) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate (twice). The obtained organic layer was washed successively with water (twice) and saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the solvent in the filtrate was evaporated to give the title compound (179 mg).

Workup

  1. extractionextracted with ethyl acetate (twice)
  2. washThe obtained organic layer was washed successively with water (twice) and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. customthe solvent in the filtrate was evaporated

Sources & evidence

ORD record
ord-9496a8ac587f42f9b99c088d45816380
Source dataset
uspto-grants-2015_05
Patent number
US09040717B2

Reaction notes

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