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 469500노트

반응식

HRID 469500 반응식
[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]

참가 물질

4

반응물 2

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

생성물 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 bromide수율 51.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ad7da706477a4d9c99ee775562fa159a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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