Tetrahydrofuran → HCID 23114765, compound

HRID 2080521Notes

Reaction equation

HRID 2080521 reaction equation
O1CCCC1.[Cl:6][CH2:7][CH2:8][CH2:9][S:10]([N:13]([C:21]1[CH:26]=[C:25]([CH:27]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C:24]([Cl:46])=[CH:23][N:22]=1)S(CCCCl)(=O)=O)(=[O:12])=[O:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>CCCCCC>[Cl:6][CH2:7][CH2:8][CH2:9][S:10]([NH:13][C:21]1[CH:26]=[C:25]([CH:27]([S:36]([C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)(=[O:37])=[O:38])[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C:24]([Cl:46])=[CH:23][N:22]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 23114733HCID 23114733, compound

Product 1

HCID 23114765HCID 23114765, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a tetrahydrofuran (5 ml) solution of 3-chloro-N-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]-N-(3-chloropropylsulfonyl)propane-1-sulfonamide (193 mg, 0.272 mmol) was added to a tetrahydrofuran solution (11.0M, 0.28 ml, 0.28 mmol) of tetrabutylammonium fluoride. The resulting mixture was stirred at room temperature for 1 hour. 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 (=4:1) eluate was concentrated under reduced pressure to give the title compound (108 mg, 0.190 mmol, 70%) as a white solid.

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. concentrationethyl acetate (=4:1) eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ad0dd70f23c34e909bab8eafb5964116
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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