Tetrabutylammonium Fluoride → HCID 58932222, compound

HRID 854208Notes

Reaction equation

HRID 854208 reaction equation
C([Si](CC)(C(C)C)[O:4][CH:5]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH:14]([O:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[CH2:24][CH2:23]2)=[O:21])[CH:13]=[CH:12][CH:11]([CH3:35])[CH:10](/[C:36](/[CH3:61])=[CH:37]/[CH:38]=[CH:39]/[C:40]([OH:60])([CH3:59])[CH2:41][CH:42]2[O:58][CH:43]2[CH:44]([CH3:57])[CH:45]([O:48][Si](CC)(CC)C(C)C)[CH2:46][CH3:47])[O:9][C:7](=[O:8])[CH2:6]1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:4][CH:5]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH:14]([O:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)[CH2:24][CH2:23]2)=[O:21])[CH:13]=[CH:12][CH:11]([CH3:35])[CH:10](/[C:36](/[CH3:61])=[CH:37]/[CH:38]=[CH:39]/[C:40]([OH:60])([CH3:59])[CH2:41][CH:42]2[O:58][CH:43]2[CH:44]([CH3:57])[CH:45]([OH:48])[CH2:46][CH3:47])[O:9][C:7](=[O:8])[CH2:6]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58932209HCID 58932209, compound

Product 1

HCID 58932222HCID 58932222, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (8E,12E,14E)-3,21-bis(diethylisopropylsiloxy)-16-hydroxy-6,10,12,16,20-pentamethyl-7-((4-(1-methylpiperidin-4-yl)piperazin-1-yl)carbonyl)oxy-18,19-epoxytricosa-8,12,14-trien-11-olide (18.5 mg, 19.2 μmol) in tetrahydrofuran (2 mL) was cooled to 5° C. Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 42.3 μL, 42.3 μmol) was added dropwise to the solution, and the reaction mixture was stirred at room temperature for four hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with an aqueous solution of sodium hydrogencarbonate. The resulting organic layer was washed with an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, filtered concentrated under reduced pressure. The resulting residue was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; methanol-dichloromethane, 1:24) to obtain the title compound (7.6 mg, 56%) as a colorless oil.

Workup

  1. washthe organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  2. washThe resulting organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; methanol-dichloromethane, 1:24)

Sources & evidence

ORD record
ord-9558b27cc4eb4988ad98d0f1151b3418
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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