Methanol → 1-t-butoxycarbonyl-4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 1584450노트

반응식

HRID 1584450 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C)C)[C:18]3[CH:30]=[CH:31][CH:32]=[CH:33][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[F-].[NH4+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][OH:22])[C:18]3[CH:30]=[CH:31][CH:32]=[CH:33][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 25516Ammonium fluorideHCID 18464522HCID 18464522, 화합물

생성물 1

HCID 184648041-t-butoxycarbonyl-4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Combine 1-(t-butoxycarbonyl)-4-(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (4.22 g, 8.88 mmol), and methanol (60 mL). Add ammonium fluoride (1.97 g, 53.3 mmol). Heat to reflux. After 2 hours, cool the reaction mixture and partition between dichloromethane (300 mL) and a saturated aqueous solution of sodium bicarbonate (200 mL). Separate the layers and extract the organic layer three times with water and then brine. 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-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.32 (silica gel, ethyl acetate).

후처리

  1. temperatureHeat to reflux
  2. temperaturecool the reaction mixture
  3. custompartition between dichloromethane (300 mL)
  4. customSeparate the layers
  5. extractionextract the organic layer three times with water
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

출처 및 근거

ORD 기록
ord-92d2ecba49bf411095433d2203e437ac
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932571

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