Azobisisobutyronitrile → HCID 90327418、化合物

HRID 1471630ノート

反応式

HRID 1471630 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:30])[C:10](=[O:29])[C@@H:11]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH2:20])[CH:14]=2)=[CH:5][CH:4]=1.[C:31]([OH:34])(=[S:33])[CH3:32].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[C:31](=[O:34])([S:33][CH2:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][C@H:11]([NH:21][C:22]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28])[C:10]([N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:30])=[O:29])[CH:14]=1)[CH3:32]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 90289950HCID 90289950、化合物HCID 178418634HCID 178418634、化合物

生成物 1

HCID 90327418HCID 90327418、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

To a solution of (5)-tert-butyl 1-((4-methoxyphenyl)(methyl)amino)-1-oxo-3-(3-vinylphenyl)propan-2-ylcarbamate (2.9 g, 7.06 mmol) and thioacetic acid (5 ml) in toluene (30 ml), was added azobisisobutyronitrile, (3.2 ml, 0.2M in toluene) dropwise. The solution was degassed for 30 minutes by purging with nitrogen. After purging was complete, the reaction was heated at 100° C. for 2 hours. The reaction was cooled to room temperature and then diluted with EtOAc (100 ml). The organics were washed with sodium bicarbonate (3×). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (20-50% EtOAc/hexanes) to provide the desired product (2.8 g, 5.74 mmol), 81.4%. MS (m/z) 487 [M+H]+.

後処理

  1. customThe solution was degassed for 30 minutes
  2. customby purging with nitrogen
  3. customAfter purging
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with EtOAc (100 ml)
  6. washThe organics were washed with sodium bicarbonate (3×)
  7. dry with materialThe organic layer was dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe crude product was introduced to a silica gel loading column
  11. custompurified by column chromatography (20-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-e6bec8f775564ad992548fa997809f27
出典データセット
uspto-grants-2015_04
特許番号
US09012441B2

反応ノート

読み込み中…