4-Fluoro-2-hydroxyphenacyl bromide → (R)-1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 453692

반응식

HRID 453692 반응식
[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[OH:37])=[O:29]>CCOC(C)=O.C(#N)C>[Br-:26].[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:28](=[O:29])[CH2:27][N+:13]23[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]2)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12]3)=[C:31]([OH:37])[CH:32]=1

참가 물질

5

반응물 2

HCID 269860714-Fluoro-2-hydroxyphenacyl bromideHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

생성물 1

HCID 86660302(R)-1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide수율 91%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (100 mg, 0.30 mmol) in EtOAc (3 ml) and acetonitrile (2 ml), was added 2-bromo-1-(4-fluoro-2-hydroxyphenyl)ethanone (69.3 mg, 0.30 mmol), and the reaction was stirred at room temperature for 15 hours (UPLC-MS: complete conversion). The solvent was evaporated and the crude was triturated in i-Pr2O-EtOAc (1/1) to obtain (R)-1-(2-(4-fluoro-2-hydroxyphenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (154.0 mg, 91% yield).

후처리

  1. customThe solvent was evaporated
  2. customthe crude was triturated in i-Pr2O-EtOAc (1/1)

출처 및 근거

ORD 기록
ord-34f9f34d961a4db9a2ab4b5197a10bec
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492548B2

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