Water → Tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamate

HRID 1382928ノート

反応式

HRID 1382928 の反応式
[CH3:1][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[CH2:3].CS(O[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=O)=O.O>CN(C)C=O>[CH3:3][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5]1=[O:13])=[CH2:1]

参加物

5

反応物 3

HCID 962WaterHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 184654786-((tert-Butoxycarbonyl)amino)hexyl methanesulfonate

生成物 1

HCID 57066051Tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamate収率 94.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

5.9 g (135 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane and subsequently covered with 100 ml of dimethylformamide. To this suspension are added dropwise at room temperature 22.3 g (128 mmol) of 1-(1-methylvinyl)benzimidazolin-2-one in 100 ml of dimethylformamide. After stirring at room temperature for 2 hours 55.0 g of tert.-butyl [6-[(methylsulphonyl)oxy]hexyl]carbamate in 100 ml of dimethylformamide are added dropwise and the reaction mixture is stirred at room temperature for 18 hours. Thereafter. the reaction mixture is poured into 1 l of water and extracted with 750 ml of methylene chloride. The organic extract is washed with water, dried over potassium carbonate and evaporated. The thus-obtained residue is chromatographed on 950 g of silica gel with methylene chloride/hexane, methylene chloride and a 95:5 mixture of methylene chloride and isopropanol as the elution agent, whereby there are obtained 45.3 g of tert.-butyl [6-[3-(1-methylvinyl)-2-oxo-1-benzimidazolinyl]hexyl]carbamate as an oil.

後処理

  1. wash5.9 g (135 mmol) of a 55% sodium hydride dispersion in mineral oil are washed oil-free with hexane
  2. additionare added dropwise
  3. extractionextracted with 750 ml of methylene chloride
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over potassium carbonate
  7. customevaporated
  8. customThe thus-obtained residue is chromatographed on 950 g of silica gel with methylene chloride/hexane, methylene chloride
  9. additiona 95:5 mixture of methylene chloride and isopropanol as the elution agent, whereby there

出典と根拠

ORDレコード
ord-460071627ed44ef7818bfec8e837ad93
出典データセット
uspto-grants-1989_02
特許番号
US04808605

反応ノート

読み込み中…