3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 54766236, Verbindung

HRID 1044069

Reaktionsgleichung

Reaktionsgleichung von HRID 1044069
[Cl:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][N:4]=1.[C:14]1([CH:20]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[C:21]([O:23][C@@H:24]2[CH:29]3[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]3)[CH2:25]2)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C.C(OCC)(=O)C>[Cl-:1].[C:8]1([C:6]2[O:5][N:4]=[C:3]([CH2:2][N+:26]34[CH2:27][CH2:28][CH:29]([CH2:30][CH2:31]3)[C@@H:24]([O:23][C:21](=[O:22])[CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[CH2:25]4)[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

Produkt 1

HCID 54766236HCID 54766236, VerbindungAusbeute 19,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (79 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate (I23) (129 mg, 0.37 mmol) in acetonitrile (1.2 ml) and ethyl acetate (2.4 ml). The yellow solution was stirred at room temperature for 48 hours. The solution was evaporated, and the residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-1-((5-phenyl-1,2,4-oxadiazol-3-yl)methyl)-3-(2-phenyl-2-(o-tolylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (39 mg, 19% yield, mixture of diastereomers).

Aufarbeitung

  1. customThe solution was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-e0eddd1fcbfc4ded98c93537f94d1c73
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563577B2

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