Bromoacetonitrile → HCID 18464492、化合物

HRID 637082ノート

反応式

HRID 637082 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

HCID 18464492HCID 18464492、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9e3286d1560b46b696168f48721dbc7a
出典データセット
uspto-grants-2001_02
特許番号
US06194406B1

反応ノート

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