2-Butene, 1-bromo-3-methyl- → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469504노트

반응식

HRID 469504 반응식
[Br:1][CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]([NH:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16](=[O:26])[O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[CH:11][CH:10]=1>CCOC(C)=O>[Br-:1].[CH2:34]([O:33][C:31]([C:30]1[CH:29]=[C:28]([NH:27][CH:15]([C:12]2[CH:13]=[N:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[C:16]([O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N+:20]([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])([CH2:21][CH2:22]3)[CH2:19]2)=[O:26])[CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:35]

참가 물질

4

반응물 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

생성물 1

HCID 67124898(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide수율 86.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1-Bromo-3-methylbut-2-ene (16.9 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. 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-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide (56 mg, 84% 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-7f5d8f9f91ea4544ad1011ac3d5f8a6e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

반응 노트

불러오는 중…