2-(Chloroacetyl)thiophene → 3-((Bis(4-chlorophenyl)methoxy)-carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1910505

반응식

HRID 1910505 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:10])[CH2:2]2.Cl[CH2:28][C:29]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)=[O:30]>CCOC(C)=O>[Cl-:19].[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29](=[O:30])[C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70925824Bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate

생성물 1

HCID 866729443-((Bis(4-chlorophenyl)methoxy)-carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride수율 52.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of bis(4-chlorophenyl)methyl quinuclidine-3-carboxylate (45 mg, 0.11 mmol, prepared as in example 6) in EtOAc (1.6 ml), 2-chloro-1-(thiophen-2-yl)ethanone (20.0 mg, 0.13 mmol) was added. The reaction was stirred at room temperature for 16 hours. Solvent was removed, and the crude was purified by preparative HPLC to afford 3-((bis(4-chlorophenyl)methoxy)-carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (16 mg, racemic mixture).

후처리

  1. customSolvent was removed
  2. customthe crude was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e6c122cd3ca0450da188b0294fb5f96c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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