Methyl iodide → benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}methylcarbamate

HRID 1881463노트

반응식

HRID 1881463 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:12]2[N:13]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])[CH:14]=[C:15]([CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][CH3:20])[N:16]=2)=[CH:6][CH:5]=1.[CH3:40]I>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([N:29]([CH3:40])[C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:12]2[N:13]([S:23]([N:26]([CH3:28])[CH3:27])(=[O:24])=[O:25])[CH:14]=[C:15]([CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][CH3:20])[N:16]=2)=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86637798benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate

생성물 1

HCID 86637799benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}methylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Sodium hydride (60 wt % in mineral oil) (69 mg, 1.15 mmol) was added to a 0° C. solution of benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate (340 mg, 0.58 mmol) in tetrahydrofuran (6 mL). After stirring at 0° C. for 20 min, methyl iodide (72 μL, 1.15 mmol) was added and the reaction allowed to warm to ambient temperature. The reaction mixture was quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}methylcarbamate.

후처리

  1. temperatureto warm to ambient temperature
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride and ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-141acb41dbb54ee7b9b715c8d08bbe65
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318767B2

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