Hydrochloric Acid → HCID 178438664, Verbindung

HRID 1412317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412317
C(O[C:4](=[O:41])[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18](=[O:19])[C:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]#[N:34])=[CH:23][CH:22]=3)=[C:16]([CH2:35][CH2:36][CH3:37])[N:15]3[N:38]=[CH:39][N:40]=[C:14]23)[CH2:9][CH2:8]1)C.[CH2:42]([Mg]Br)[CH3:43].Cl.O1CC[CH2:49][CH2:48]1>>[CH2:48]([C:4]([OH:41])([CH2:42][CH3:43])[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:18](=[O:19])[C:17]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:25][CH:26]=3)=[C:16]([CH2:35][CH2:36][CH3:37])[N:15]3[N:38]=[CH:39][N:40]=[C:14]23)[CH2:9][CH2:8]1)[CH3:49]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 178418443HCID 178418443, VerbindungHCID 178438680HCID 178438680, Verbindung

Produkt 1

HCID 178438664HCID 178438664, VerbindungAusbeute 49 %

Versuchsvorschrift

Ethyl[(trans-4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]acetate (0.5 g) was dissolved in tetrahydrofuran (10 mL), and ethylmagnesium bromide (3.0 M diethyl ether solution, 0.75 mL) was added at 0° C. After stirring at the same temperature for 16 hr, 1 N hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.25 g, 49%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bcfa28b42ce649ddbc33021d8616c810
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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