Tetrabutylammonium Fluoride → HCID 57197061, compound

HRID 1955432Notes

Reaction equation

HRID 1955432 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 (0.01 8 mmol) of a 1.0M solution of tetrabutylammonium 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-19094f4185c6447fb1f861ae8d5e61a9
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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