Ethyl 4-(2-bromoacetyl)benzoate → HCID 86660305, Verbindung

HRID 453695

Reaktionsgleichung

Reaktionsgleichung von HRID 453695
[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:40]=[CH:39][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][CH:31]=1)=[O:29]>CCOC(C)=O>[Br-:26].[CH2:37]([O:36][C:34]([C:33]1[CH:39]=[CH:40][C:30]([C:28](=[O:29])[CH2:27][N+:13]23[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]2)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]3)=[CH:31][CH:32]=1)=[O:35])[CH3:38]

Komponenten

4

Edukt 2

HCID 11966043Ethyl 4-(2-bromoacetyl)benzoateHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Produkt 1

HCID 86660305HCID 86660305, VerbindungAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in EtOAc (5 ml), was added ethyl 4-(2-bromoacetyl)benzoate (I12) (66.5 mg, 0.24 mmol), and the reaction was stirred at room temperature for 15 hours. The solvent was evaporated and the crude was triturated with i-Pr2O-EtOAc (1/1) to obtain (R)-1-(2-(4-(ethoxycarbonyl)phenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (128.5 mg, 95% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude was triturated with i-Pr2O-EtOAc (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-000d5adec3184a90a8dea6a61c934f3f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492548B2

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