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

HRID 1619513노트

반응식

HRID 1619513 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33]>CCOC(C)=O>[Br-:30].[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:20][CH2:19][N+:18]([CH2:31][C:32](=[O:33])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH2:23][CH2:22]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 6259Phenacyl bromideHCID 67605836(R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate

생성물 1

HCID 86665824(3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 85.9%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate (C29) (100 mg, 0.25 mmol) in EtOAc (5 ml), was added 2-bromo-1-phenylethanone (55.5 mg, 0.28 mmol), and the reaction was stirred at RT for 15 hours. The solvent was evaporated, and the resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7) to obtain (3R)-3-(2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (127.5 mg; 85% yield).

후처리

  1. customThe solvent was evaporated
  2. customthe resulting crude was purified by silica gel flash chromatography (DCM/MeOH=93/7)

출처 및 근거

ORD 기록
ord-832868ce819e42c5925cfede09345cf3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772314B2

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