Trifluoroacetic acid → HCID 23114806, compound

HRID 2080522Notes

Reaction equation

HRID 2080522 reaction equation
[Cl:1][C:2]1[C:3]([CH:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:4][C:5]([N:8](S(C(F)(F)F)(=O)=O)[S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[N:6][CH:7]=1.O.[OH-].[Li+].[Cl-].[NH4+].FC(F)(F)C(O)=O>O1CCCC1.O.CCOCC.C(OCC)(=O)C.CCCCCC>[Cl:1][C:2]1[C:3]([CH:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:33])=[O:34])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:4][C:5]([NH:8][S:9]([C:12]([F:13])([F:14])[F:15])(=[O:11])=[O:10])=[N:6][CH:7]=1

Participants

10

Reactant 4

HCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 23114739HCID 23114739, compound

Product 1

HCID 23114806HCID 23114806, compoundYield 63%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]-N-(trifluoromethylsulfonyl)trifluoromethanesulfonamide (77 mg, 0.111 mmol) in a mixture of tetrahydrofuran (5 ml) and water (1 ml) was added lithium hydroxide monohydrate (5.0 mg, 0.111 mmol). The resulting mixture was stirred at room temperature for 5 hours. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate containing 0.5% trifluoroacetic acid was concentrated under reduced pressure. To the residue thus obtained was added ether, and the solid thus precipitated was collected by filtration to give the title compound (39 mg, 0.069 mmol, 63%) as a white powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationwas concentrated under reduced pressure
  8. customTo the residue thus obtained
  9. customthe solid thus precipitated
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-93fb36222bad413b80ee6c456e9825d4
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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