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 469500ノート

反応式

HRID 469500 の反応式
[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]

参加物

4

反応物 2

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

生成物 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 bromide収率 51.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ad7da706477a4d9c99ee775562fa159a
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

読み込み中…