2-Chloro-N-pyridin-2-yl-acetamide → (R)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 453697

Reaktionsgleichung

Reaktionsgleichung von HRID 453697
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:4].[C:12]1([C@@H:18]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:19]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O>[Cl-:1].[O:4]=[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:2][N+:24]12[CH2:25][CH2:26][CH:27]([CH2:28][CH2:29]1)[C@@H:22]([O:21][C:19](=[O:20])[C@@H:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:23]2

Komponenten

4

Edukt 2

HCID 2894352-Chloro-N-pyridin-2-yl-acetamideHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Produkt 1

HCID 86660307(R)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chlorideAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-N-(pyridin-2-yl)acetamide (30.4 mg, 0.18 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (60 mg, 0.18 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight (UPLC-MS: complete conversion). The solvent was evaporated, and the crude rodcut was triturated with Et2O (2 ml). The product was further purified by preparative HPLC to obtain (R)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane chloride (34.5 mg, 38.2% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude rodcut was triturated with Et2O (2 ml)
  3. customThe product was further purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-82dc2db5027a4a3cbc0aaea1a0156700
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492548B2

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