Tetrabutylammonium Fluoride → HCID 87593948, compound

HRID 626651Notes

Reaction equation

HRID 626651 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([NH2:24])=[N:18][C:19]=3[Cl:23])[C:11](=[CH2:25])[C@@H:10]1[CH2:26][O:27][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:23][C:19]1[N:18]=[C:17]([NH2:24])[N:16]=[C:15]2[C:20]=1[N:21]=[CH:22][N:14]2[C@H:12]1[CH2:13][C@H:9]([OH:8])[C@@H:10]([CH2:26][OH:27])[C:11]1=[CH2:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 87593598HCID 87593598, compound

Product 1

HCID 87593948HCID 87593948, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.38 mmol) Compound 24 was dissolved in 10 ml THF, to which 720 mg TBAF (tetrabutylammonium fluoride) (6 mmol) was added. The mixture was stirred at room temperature for 1 hour. TLC showed the dot of starting material disappeared. THF was evaporated off under reduced pressure. 40 ml EtOAc was added to the residue. The mixture was successively washed with 20 ml water and saturated NaCl solution, dried with anhydrous Na2SO4, and filtered. The filtrate was evaporated to dryness under reduced pressure, to afford 52 mg (47%) of title compound as light yellow solid.

Workup

  1. additionwas added
  2. customTHF was evaporated off under reduced pressure
  3. addition40 ml EtOAc was added to the residue
  4. washThe mixture was successively washed with 20 ml water and saturated NaCl solution
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c6a80d1186984a64a1a3231e87a06c15
Source dataset
uspto-grants-2016_04
Patent number
US09309249B2

Reaction notes

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