Tetrabutylammonium Fluoride → HCID 71293508, compound

HRID 2362306Notes

Reaction equation

HRID 2362306 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H: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[C@@H: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 71293438HCID 71293438, compound

Product 1

HCID 71293508HCID 71293508, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Intermediate 27 (620 mg, 0.85 mmol) was dissolved in THF (7 mL), and then a solution of 1 M TBAF in THF (1.3 ml, 1.3 mmol) was added. The reaction mixture was stirred at RT for 16 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 4-5% methanol in DCM to afford the title compound as a colourless oil (476 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 4-5% methanol in DCM

Sources & evidence

ORD record
ord-9279b4c96adf4bbc8097567119761cab
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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