Tetrabutylammonium Fluoride → HCID 57197061, compound

HRID 1275409Notes

Reaction equation

HRID 1275409 reaction equation
[CH3:1][C:2]([CH3:50])([CH3:49])[C@H:3]([NH:7][C:8](=[O:48])[C@@H:9]([CH2:17][C@@H:18]([O:40][Si](C(C)(C)C)(C)C)[CH2:19][S:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4](C)=[O:5].[F-].[CH2:52]([N+:56](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOCC>[CH3:50][C:2]([CH3:1])([CH3:49])[C@H:3]([NH:7][C:8](=[O:48])[C@@H:9]([CH2:17][C@@H:18]([OH:40])[CH2:19][S:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4](=[O:5])[NH:56][CH3:52]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57022915HCID 57022915, compound

Product 1

HCID 57197061HCID 57197061, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.13 g (7.027 mmol) of the product of Example 29 dissolved in 75 mL of THF was added 17.6 mL (0.018 mmol) of a 1.0M solution of tetrabutylarnmonium fluoride in THF. The reaction mixture was stirred at room temperature for 4 h and then diluted with ether. The resulting solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc/Hexanes (gradient: 1:3-1:1) to provide 2.78 g (64%) of the desired product as a colorless oil. Electrospray Mass Spec: 617.5 (M+H)+.

Workup

  1. washThe resulting solution was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with EtOAc/Hexanes (gradient: 1:3-1:1)

Sources & evidence

ORD record
ord-b7ed5dcb9c414f3c8d69635d3e56f812
Source dataset
uspto-grants-2000_12
Patent number
US06160132

Reaction notes

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