Tetrabutylammonium Fluoride → HCID 69216577, compound

HRID 272752Notes

Reaction equation

HRID 272752 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:28]2[S:29][CH:30]=[C:31]([Si](C)(C)C)[N:32]=2)[OH:27])=[C:22]([O:37][CH3:38])[CH:21]=1>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[OH:27])=[C:22]([O:37][CH3:38])[CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69216435HCID 69216435, compound

Product 1

HCID 69216577HCID 69216577, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.58 mL, IM solution in THF) was added to a solution of Example 685A (96 mg, 0.29 mmol) in THF (2 mL). The resulting solution was stirred at room temperature for 1 hour. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by preparative HPLC to provide 65 mg (88%) of the title compound. MS (ESI) m/e 256 (M+H)+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-96e4663f1d744f90a11e4c2b19da9cc1
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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