Ethyl Acetate → HCID 18464522, 화합물

HRID 2230698노트

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HRID 2230698 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Si:26]([O:33][CH2:34][CH2:35]I)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:35][CH2:34][O:33][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

생성물 1

HCID 18464522HCID 18464522, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (3.06 g, 9.67 mmol) and sodium hydride (0.43 g, 60% in oil, 10.64 mmol) in tetrahydrofuran (60 mL) and dimethylformamide (6 mL). After 2 hours, add 2-(t-butyldimethylsilyloxy)ethyl iodide (2.78 g, 9.67 mmol). After 20 hours, heat to reflux. After 4 hours, cool to ambient temperature and add ice to quench. Evaporate in vacuo to remove most of the tetrahydrofuran. Partition the evaporated reaction mixture between ethyl acetate (250 mL) and water (200 mL). Separate the layers and extract the organic layer with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give 1-(t-butoxycarbonyl)-4-(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.58 (silica gel, ethyl acetate).

후처리

  1. waitAfter 20 hours
  2. temperatureheat to reflux
  3. waitAfter 4 hours
  4. additionadd ice
  5. customto quench
  6. customEvaporate in vacuo
  7. customto remove most of the tetrahydrofuran
  8. customPartition
  9. customthe evaporated reaction mixture between ethyl acetate (250 mL) and water (200 mL)
  10. customSeparate the layers
  11. extractionextract the organic layer with water
  12. dry with materialDry the organic layer over MgSO4
  13. filtrationfilter
  14. customevaporate in vacuo
  15. customto give a residue

출처 및 근거

ORD 기록
ord-c5d72ce9220a4ff7b0c72fcd16fa3e08
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423704B1

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