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Water → HCID 10274305, Verbindung

HRID 1829801
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1829801
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C@H:26]([C@H:28]([N:36]1[CH:40]=[C:39]([C:41]([NH2:43])=[O:42])[N:38]=[CH:37]1)[CH2:29][CH2:30]OS(C)(=O)=O)[CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:25][C@H:26]([C@H:28]([N:36]1[CH:40]=[C:39]([C:41]([NH2:43])=[O:42])[N:38]=[CH:37]1)[CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 111649271-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide

Produkt 1

HCID 10274305HCID 10274305, VerbindungAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Under N2, to a solution of 6-hydroxyquinoline (43 mg, 0.296 mmol) in DMF (3 ml) was added potassium carbonate (82 mg, 0.593 mmol) at room temperature. The reaction mixture was stirred for 30 minutes. 1-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide was added and the resulting mixture was stirred for 6 h at 70° C. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (8 g) chromatography eluting with chloroform/methanol (100:1 to 30:1) to give 1-[(2S,3R)-2-benzyloxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (1) (62.5 mg, 48.9%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 6 h at 70° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel (8 g) chromatography
  7. washeluting with chloroform/methanol (100:1 to 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-b6b01da65d2d42bd83c4e36ff946cf1e
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07064144B2

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