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Water → HCID 58452767, Verbindung

HRID 70625
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 70625
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[NH:27][C:26](=[O:28])[C:25]([Cl:29])=[CH:24][CH:23]=2)=[CH:15][C@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)=[CH:10][CH:9]=1.O.[Cl-].[NH4+]>C(#N)C>[Cl:29][C:25]1[C:26](=[O:28])[NH:27][C:22](/[C:14](/[C:11]2[CH:12]=[CH:13][C:8]([CH2:7][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)=[CH:15]/[C@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)=[CH:23][CH:24]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 31268PyrrolidineHCID 673960336-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one

Produkt 1

HCID 58452767HCID 58452767, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

Separately, pyrrolidine (0.424 mL) was added to a solution of 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one (E:Z=1:2 mixture) (206 mg) in acetonitrile (8.24 mL) at room temperature, and the mixture was stirred at room temperature for one hour. Water and a saturated ammonium chloride solution were sequentially added to the reaction solutions at room temperature, and the mixtures were combined, followed by extraction with chloroform. The organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=5:1) to give the title compound as a white solid (70 mg, 30%).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative TLC (chloroform:methanol=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d3e64fa0f513486f8b06c29c4a0222c5
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822503B2

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