2-Bromo-1-(4-hydroxyphenyl)ethanone → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469500
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][O:13][C:14]1[N:19]=[CH:18][C:17]([CH:20]([NH:32][C:33]2[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=2)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:21](=[O:31])[O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[CH:16][CH:15]=1>CCOC(C)=O>[Br-:1].[CH2:39]([O:38][C:36]([C:35]1[CH:34]=[C:33]([NH:32][CH:20]([C:17]2[CH:18]=[N:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[C:21]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N+:25]([CH2:2][C:3]([C:5]4[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=4)=[O:4])([CH2:26][CH2:27]3)[CH2:24]2)=[O:31])[CH:43]=[CH:42][CH:41]=1)=[O:37])[CH3:40]

Komponenten

4

Edukt 2

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Produkt 1

HCID 86660335(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Bromo-1-(4-hydroxyphenyl)ethanone (24.5 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 was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide (37.3 mg, 50.1% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-ad7da706477a4d9c99ee775562fa159a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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