Tetrabutylammonium Fluoride → HCID 21875586, Verbindung

HRID 858447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858447
[Si]([O:8][C:9]1[CH:41]=[CH:40][C:12]2[N:13]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=3)[C:14]([CH2:16][CH3:17])=[N:15][C:11]=2[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:16]([C:14]1[N:13]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=2)[C:12]2[CH:40]=[CH:41][C:9]([OH:8])=[CH:10][C:11]=2[N:15]=1)[CH3:17]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67098924HCID 67098924, Verbindung

Produkt 1

HCID 21875586HCID 21875586, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-2-ethyl-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-benzimidazole (step 5, 78 mg, 0.13 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF, 0.16 mL, 0.16 mmol) at 0° C. The mixture was stirred at 0° C. for 2.5 h, then concentrated. The residue was dissolved in water (30 mL) and extracted with dichloromethane (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1) to afford 57 mg (92%) of the title compound as white amorphous: MS (ESI) m/z 479 (M+H)+;

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with dichloromethane (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol (gradient elution from 20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-6590dff8e85d4c679b1ba5cf505a497a
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148234B2

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