Tetrabutylammonium Fluoride → HCID 71293490, compound

HRID 570875Notes

Reaction equation

HRID 570875 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:39])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C)(=[O:27])=[O:26])[N:21]=[C:8]2[N:7]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=2)[C:6]=1[CH3:50])=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[N:9]2[C:19](=[O:39])[N:20]([CH2:22][CH2:23][CH2:24][S:25]([CH2:28][CH2:29][CH2:30][OH:31])(=[O:26])=[O:27])[N:21]=[C:8]2[N:7]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:48])([F:47])[F:49])[CH:41]=2)[C:6]=1[CH3:50])=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71293416HCID 71293416, compound

Product 1

HCID 71293490HCID 71293490, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Intermediate 21 (282 mg, 0.38 mmol) was dissolved in THF (3 mL), and then a solution of 1 M TBAF in THF (760 μl, 0.76 mmol) was added. The reaction mixture was stirred at RT for 4 hours and then partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-2% methanol in EtOAc to afford the title compound (89 mg).

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer further extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0-2% methanol in EtOAc

Sources & evidence

ORD record
ord-1e08e5ff805443df8f51d73d4dc609fb
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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