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

HRID 425382ノート

反応式

HRID 425382 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c72e15323724fa3901ce8e2e1962fda
出典データセット
uspto-grants-2012_01
特許番号
US08106070B2

反応ノート

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