Hydrogen Bromide → 6-{(Z)-1-Bromo-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one
Reaktionsgleichung
Br.[Br:2]/[C:3](/[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18]C)[N:12]=1)=[CH:4]\[C@@H:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.O>O1CCOCC1>[Br:2]/[C:3](/[C:11]1[NH:12][C:13](=[O:18])[C:14]([Cl:17])=[CH:15][CH:16]=1)=[CH:4]\[C@H:5]1[CH2:6][CH2:7][C:8](=[O:10])[NH:9]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
48% hydrobromic acid (2 mL) was added to a solution of (5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (115 mg) in 1,4-dioxane (3 mL), and the mixture was stirred at 65° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1) to give the title compound as a colorless powder (40 mg, 37%).
Aufarbeitung
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was then evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-d463d54529ec456088cf0930fbb68622
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08822503B2
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