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Potassium Carbonate → HCID 58355468, Verbindung

HRID 1509470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1509470
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11](Cl)(Cl)Cl)[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[C:7]=2[CH:21]=1.[CH3:22][CH:23]([CH3:43])[CH2:24][NH:25][C@@H:26]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][C@H:28]([C:39]([O:41]C)=[O:40])[CH2:27]1.C(=O)([O-])[O-:45].[K+].[K+]>C(#N)C.O>[C:35]([O:34][C:32]([N:30]1[CH2:31][C@@H:26]([N:25]([C:11]([C:9]2[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[C:7]3[CH:21]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[N:10]=2)=[O:45])[CH2:24][CH:23]([CH3:43])[CH3:22])[CH2:27][C@@H:28]([C:39]([OH:41])=[O:40])[CH2:29]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 583557496-methoxy-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazoleHCID 593566071-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

Produkt 1

HCID 58355468HCID 58355468, VerbindungAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917
Acetonitrile--water (1/1)
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-Methoxy-1-(4-methoxybutyl)-2-(trichloromethyl)-1H-benzimidazole (1.42 g) was dissolved in acetonitrile-water (2:1, 150 ml), 1-tert-butyl 3-methyl (3R,5S)-5-{(2-methylpropyl)amino}piperidine-1,3-dicarboxylate (1.02 g) was added, potassium carbonate (5.5 g) was added and the mixture was stirred at 80° C. for 19 hr. The reaction mixture was concentrated under reduced pressure, acidified (pH 3) with 6M hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (5:95)-ethyl acetate-ethyl acetate-methanol (85:15) was concentrated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and a fraction eluted with water-acetonitrile (9:1-6:4) was collected, basified (pH 10) with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object product (460 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (5:95)-ethyl acetate-ethyl acetate-methanol (85:15)
  6. concentrationwas concentrated under reduced pressure
  7. washa fraction eluted with water-acetonitrile (9:1-6:4)
  8. customwas collected
  9. extractionextracted with ethyl acetate
  10. dry with materialThe extract was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-44f194c8ab60461ca47a66e8eb7f7e7e
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221836B2

Notizen zur Reaktion

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