Tetrabutylammonium Fluoride → HCID 178464132, compound

HRID 1170441Notes

Reaction equation

HRID 1170441 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:38][Si](CC)(CC)CC)[C:17]2[C:12](=[CH:13][C:14]([C:22]3[O:23][CH:24]=[CH:25][N:26]=3)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:27][C@H:28]2[CH2:31][C@H:30]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:29]2)[C:10]1=[O:37].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:38])[C:17]2[C:12](=[CH:13][C:14]([C:22]3[O:23][CH:24]=[CH:25][N:26]=3)=[CH:15][C:16]=2[C:18]([F:19])([F:20])[F:21])[N:11]([CH2:27][C@H:28]2[CH2:29][C@H:30]([N:32]([CH2:33][CH3:34])[CH2:35][CH3:36])[CH2:31]2)[C:10]1=[O:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178464148HCID 178464148, compound

Product 1

HCID 178464132HCID 178464132, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 14-2 (160 mg, 0.234 mmol) in tetrahydrofuran (6 mL) was added tetra-n-butylammonium fluoride (100 mg, 0.383 mmol) under nitrogen, and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added, and the mixture was extracted with ethyl acetate, and then the organic layer was washed with saturated saline, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (chloroform/methanol=10/1) to give the titled compound (80 mg, 60%).

Workup

  1. additionTo the reaction solution was added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-e2e74cb88f844a25ac2149fa0d87daf5
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

Loading…