Bromoacetonitrile → HCID 18464492, 화합물

HRID 637082노트

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HRID 637082 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][OH:22])[C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:30][C:31]#[N:32].[Cl-].[NH4+]>C(OCC)(=O)C.O.CN(C)C=O.O1CCCC1>[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][CH2:30][C:31]#[N:32])[C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

9

반응물 4

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 184648041-t-butoxycarbonyl-4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

생성물 1

HCID 18464492HCID 18464492, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Combine 1-(t-butoxycarbonyl)-4-(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (1.7 g, 4.7 mmol), tetrahydrofuran (70 mL), and dimethylformamide (8 mL). Cool in an ice bath. Add with stirring, sodium hydride (0.28 9, 60% in oil, 7.0 mmol). After 3 hours, warm to ambient temperature. After 30 minutes, again cool in an ice bath and add bromoacetonitrile (1.12 g, 9.36 mmol). Warm to ambient temperature. After 18 hours, again cool in an ice bath and add a saturated aqueous solution of ammonium chloride (5 mL) and then water (5 mL). Concentrate the reaction mixture in vacuo to remove most to the tetrahydrofuran and dilute with dichloromethane (150 mL). Extract three times with water, dry the organic layer over Na2SO4, 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-cyanomethyloxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.38 (silica gel, ethyl acetate).

후처리

  1. temperatureCool in an ice bath
  2. additionAdd
  3. waitAfter 30 minutes
  4. temperatureagain cool in an ice bath
  5. temperatureWarm to ambient temperature
  6. waitAfter 18 hours
  7. temperatureagain cool in an ice bath
  8. concentrationConcentrate the reaction mixture in vacuo
  9. customto remove most to the tetrahydrofuran
  10. additiondilute with dichloromethane (150 mL)
  11. extractionExtract three times with water
  12. dry with materialdry the organic layer over Na2SO4
  13. filtrationfilter
  14. customevaporate in vacuo
  15. customto give a residue

출처 및 근거

ORD 기록
ord-9e3286d1560b46b696168f48721dbc7a
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194406B1

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