Water → HCID 86650596, compound

HRID 1257404Notes

Reaction equation

HRID 1257404 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:6]=[C:7]([C:9]#[C:10][Si](C)(C)C)[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:9]([C:7]1[CH:6]=[C:5]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:4]=[C:3]([C:2]([F:31])([F:32])[F:1])[CH:8]=1)#[CH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66939665HCID 66939665, compound

Product 1

HCID 86650596HCID 86650596, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (20 mL) of the compound (2.1 g, 4.4 mmol) obtained in Example 98a in tetrahydrofuran was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 6.5 mL, 6.5 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (940 mg, 53%) as orange crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-bf94beae4c9743d6ae1022520eae9258
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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