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 469500Notes

Reaction equation

HRID 469500 reaction equation
[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]

Participants

4

Reactant 2

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

Product 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 bromideYield 51.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ad7da706477a4d9c99ee775562fa159a
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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