Hydrochloric Acid → HCID 59492510, compound

HRID 541120Notes

Reaction equation

HRID 541120 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:17]=3[CH:16]=[C:15]([F:31])[CH:14]=2)[CH:10]=[N:9]1)(C)(C)[CH3:2].[CH:33](OCC)=[O:34].[H-].[Na+].Cl>O.C(OCC)(=O)C.O1CCCC1>[F:31][C:15]1[CH:14]=[C:13]([C:11]2[CH:10]=[N:9][N:8]([CH:7]([CH:33]=[O:34])[C:6]([O:5][CH2:1][CH3:2])=[O:32])[CH:12]=2)[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:17]=2[CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 59492525HCID 59492525, compound

Product 1

HCID 59492510HCID 59492510, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tetrahydrofuran (80 ml) and an optically active form (10.1 g) of t-butyl[4-(2-fluoro-9-hydroxy-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-acetate was added ethyl formate (4.13 ml), and the mixture was stirred at 0° C. To this mixture was added sodium hydride (60 w/w % mineral oil dispersion, 2.57 g). The reaction mixture was warmed to room temperature and stirred for 3 hr. The reaction mixture was ice-cooled, 1N hydrochloric acid was added and the mixture was stirred. Ethyl acetate and water were added thereto, and the mixture was partitioned in a separatory funnel. The aqueous layer was further extracted with ethyl acetate, and the extract was combined with the organic layer obtained earlier. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (13.2 g). The obtained residue was directly used for the next reaction without further purification.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 3 hr
  3. temperaturecooled
  4. stirringthe mixture was stirred
  5. customthe mixture was partitioned in a separatory funnel
  6. extractionThe aqueous layer was further extracted with ethyl acetate
  7. customobtained earlier
  8. washThe organic layer was successively washed with water and saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-28d39ea7718d4600b5c5f82c6f18ef34
Source dataset
uspto-grants-2014_10
Patent number
US08871934B2

Reaction notes

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