Hydrochloric Acid → HCID 46191616, compound

HRID 541130Notes

Reaction equation

HRID 541130 reaction equation
C(O)C.C([O:6][C:7](=[O:35])[CH2:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([C:16]2[C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:20]=3[CH:19]=[C:18]([CH3:34])[CH:17]=2)[CH:13]=[N:12]1)C.[OH-].[Na+].Cl>O>[OH:33][C:21]1([C:29]([F:31])([F:32])[F:30])[C:20]2[CH:19]=[C:18]([CH3:34])[CH:17]=[C:16]([C:14]3[CH:13]=[N:12][N:11]([CH2:10][CH2:9][CH2:8][C:7]([OH:35])=[O:6])[CH:15]=3)[C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 59492629HCID 59492629, compound

Product 1

HCID 46191616HCID 46191616, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethanol (5.4 ml) and an optically active form (3.55 g) of 4-[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-butyric acid ethyl ester was added 2N aqueous sodium hydroxide solution (18 ml), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was acidified with 2N hydrochloric acid (36 ml). To this mixture was added water (36 ml), and the mixture was extracted 3 times with ethyl acetate (30 ml). The combined organic layer was washed 3 times with water (50 ml) and once with saturated brine (50 ml), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (3.40 g, 100%).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate (30 ml)
  2. washThe combined organic layer was washed 3 times with water (50 ml)
  3. dry with materialonce with saturated brine (50 ml), dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3910ff652ab40e899f575fe3e7600d8
Source dataset
uspto-grants-2014_10
Patent number
US08871934B2

Reaction notes

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