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Phenacyl bromide → (3R)-3-(2-(methoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619510
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HRID 1619510 반응식
[CH3:1][O:2][C:3]([NH:5][CH:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([O:9][C@@H:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)=[O:8])=[O:4].[Br:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>CCOC(C)=O.CC#N>[Br-:24].[CH3:1][O:2][C:3]([NH:5][CH:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([O:9][C@@H:10]1[CH:15]2[CH2:16][CH2:17][N+:12]([CH2:25][C:26](=[O:27])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([CH2:13][CH2:14]2)[CH2:11]1)=[O:8])=[O:4]
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참가 물질

5

반응물 2

HCID 6259Phenacyl bromideHCID 67607568(R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate

생성물 1

HCID 86665822(3R)-3-(2-(methoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 59.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate (C26) (58.0 mg, 0.18 mmol) in EtOAc (3 ml) and CH3CN (1 ml), was added 2-bromo-1-phenylethanone (39.9 mg, 0.20 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 92/8) and the resulting product was triturated with i-Pr2O to obtain (3R)-3-(2-(methoxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (55.2 mg; 58.6% yield).

후처리

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 92/8)
  3. customthe resulting product was triturated with i-Pr2O

출처 및 근거

ORD 기록
ord-779059a821a04050aefb8c8b758180f1
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772314B2

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