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Tetrabutylammonium Fluoride → HCID 58932222, Verbindung

HRID 854208
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 854208
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 58932209HCID 58932209, Verbindung

Produkt 1

HCID 58932222HCID 58932222, VerbindungAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9558b27cc4eb4988ad98d0f1151b3418
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07256178B2

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