2-Chloroacetophenone → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469498
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16]([CH:19]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:20](=[O:30])[O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[CH:15][CH:14]=1>CCOC(C)=O>[Cl-:1].[CH2:38]([O:37][C:35]([C:34]1[CH:33]=[C:32]([NH:31][CH:19]([C:16]2[CH:17]=[N:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[C:20]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N+:24]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:25][CH2:26]3)[CH2:23]2)=[O:30])[CH:42]=[CH:41][CH:40]=1)=[O:36])[CH3:39]

Komponenten

4

Edukt 2

HCID 107572-ChloroacetophenoneHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Produkt 1

HCID 86660333(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-1-phenylethanone (17.6 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight, and then the solvent was evaporated to dryness. The residue was triturated with Et2O and then purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (26.3 mg, 38.9% yield).

Aufarbeitung

  1. customthe solvent was evaporated to dryness
  2. customThe residue was triturated with Et2O
  3. custompurified by preparative HPLC (Eluent: CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-15a58531373040699ba4e6d443a6554b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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