Tetrabutylammonium Fluoride → HCID 59750404, compound

HRID 499635Notes

Reaction equation

HRID 499635 reaction equation
[CH3:1][C:2]([CH3:31])([CH:12]([OH:30])[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[S:20][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23](=[O:25])[N:24]=2)[CH:14]=1)[C:3]([O:5]CC[Si](C)(C)C)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]([CH3:31])([CH:12]([OH:30])[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[S:20][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23](=[O:25])[N:24]=2)[CH:14]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59750466HCID 59750466, compound

Product 1

HCID 59750404HCID 59750404, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(Trimethylsilyl)ethyl 2,2-dimethyl-3-hydroxy-3-[2-(4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]propionate (0.11 g, 0.24 mmol) was dissolved in tetrahydrofuran (2 ml), and 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (0.58 ml, 0.58 mmol) was added thereto. The reaction mixture was stirred for 2 hrs and concentrated under reduced pressure. Trifluoroacetic acid (1.5 ml) was added to the residue, and the mixture was stirred at room temperature for 13 hrs. Diisopropyl ether was added to the mixture. The precipitated solid was collected by filtration and recrystallized from ethanol-hexane to give the titled compound (0.044 g, 51%) as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTrifluoroacetic acid (1.5 ml) was added to the residue
  3. stirringthe mixture was stirred at room temperature for 13 hrs
  4. additionDiisopropyl ether was added to the mixture
  5. filtrationThe precipitated solid was collected by filtration
  6. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-1b0ab6d331a648ebaf2b24e0d9ada17d
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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