Tetrabutylammonium Fluoride → HCID 58932246, compound

HRID 854204Notes

Reaction equation

HRID 854204 reaction equation
[CH3:1][C:2]([CH3:69])([CH3:68])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH:13]2[CH:14]([CH3:67])[CH2:15][CH2:16][CH:17]([O:59][Si](CC)(CC)CC)[CH2:18][C:19]([O:21][CH:22](/[C:27](/[CH3:58])=[CH:28]/[CH:29]=[CH:30]/[C:31]([CH3:57])([O:49][Si](CC)(CC)CC)[CH2:32][CH:33]3[O:48][CH:34]3[CH:35]([CH3:47])[CH:36]([O:39][Si](CC)(CC)CC)[CH2:37][CH3:38])[CH:23]([CH3:26])[CH:24]=[CH:25]2)=[O:20])=[O:11])[CH2:6][CH2:5]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:69][C:2]([CH3:1])([CH3:68])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH:13]2[CH:14]([CH3:67])[CH2:15][CH2:16][CH:17]([OH:59])[CH2:18][C:19]([O:21][CH:22](/[C:27](/[CH3:58])=[CH:28]/[CH:29]=[CH:30]/[C:31]([OH:49])([CH3:57])[CH2:32][CH:33]3[O:48][CH:34]3[CH:35]([CH3:47])[CH:36]([OH:39])[CH2:37][CH3:38])[CH:23]([CH3:26])[CH:24]=[CH:25]2)=[O:20])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86601415HCID 86601415, compound

Product 1

HCID 58932246HCID 58932246, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (8E,12E,14E)-7-((4-(2,2-dimethylpropyl)piperazin-1-yl)carbonyl)oxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (9.7 mg, 9.5 μmol) in tetrahydrofuran (1 mL) was cooled to 5° C. Tetrabutylammonium fluoride (1.0M solution in tetrahydrofuran, 31 μL, 31 μmol) was added dropwise to the reaction mixture, and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with an aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; methanol-methylene chloride, 1:49) to obtain the title compound (6.3 mg, 98%) as a colorless oil.

Workup

  1. washthe organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; methanol-methylene chloride, 1:49)

Sources & evidence

ORD record
ord-6dbaad5864ac4050abdc3878b3774dc3
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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