Trifluoroacetic acid → HCID 46191561, compound

HRID 1799009Notes

Reaction equation

HRID 1799009 reaction equation
[OH:1][C:2]1([C:30]([F:33])([F:32])[F:31])[C:14]2[CH:13]=[C:12]([CH3:15])[CH:11]=[C:10]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[CH:20]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.FC(F)(F)C(O)=O>O1CCOCC1>[OH:1][C:2]1([C:30]([F:32])([F:33])[F:31])[C:14]2[CH:13]=[C:12]([CH3:15])[CH:11]=[C:10]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:20]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59492764HCID 59492764, compound

Product 1

HCID 46191561HCID 46191561, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1,4-dioxane (6.7 ml) and an optically active form (1.34 g) of t-butyl 3-[4-(9-hydroxy-2-methyl-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-propionate was added trifluoroacetic acid (6.7 ml), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure. Toluene was added to the obtained residue and the mixture was concentrated under reduced pressure. To the residue was added water (10 ml) and the mixture was extracted twice with ethyl acetate (10 ml). The combined organic layer was washed twice with water (10 ml) and once with saturated brine (10 ml), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the obtained filtrate was concentrated under reduced pressure. Toluene was added to the obtained residue and the mixture was concentrated under reduced pressure. n-Hexane (10 ml) was added to the concentrated residue, and the slurry was stirred and filtered. The obtained solid was washed with n-hexane, and dried under reduced pressure to give the title compound (1.12 g, 96%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionToluene was added to the obtained residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue was added water (10 ml)
  5. extractionthe mixture was extracted twice with ethyl acetate (10 ml)
  6. washThe combined organic layer was washed twice with water (10 ml) and once with saturated brine (10 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationInsoluble material was filtered off
  9. concentrationthe obtained filtrate was concentrated under reduced pressure
  10. additionToluene was added to the obtained residue
  11. concentrationthe mixture was concentrated under reduced pressure
  12. additionn-Hexane (10 ml) was added to the concentrated residue
  13. stirringthe slurry was stirred
  14. filtrationfiltered
  15. washThe obtained solid was washed with n-hexane
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5fe29970f564dbd8d68eeee1a6e1368
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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