Azobisisobutyronitrile → HCID 90327418, 화합물

HRID 1471630노트

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HRID 1471630 반응식
[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]

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 90289950HCID 90289950, 화합물HCID 178418634HCID 178418634, 화합물

생성물 1

HCID 90327418HCID 90327418, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
100 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e6bec8f775564ad992548fa997809f27
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012441B2

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