Acetaldehyde → HCID 86632922, Verbindung

HRID 1628582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628582
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[OH:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:31](=O)[CH3:32].[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:35].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+].[OH-].[Na+]>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH:11]([OH:12])[C:9]1[N:8]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:7]2[C:2]([N:1]([CH2:31][CH3:32])[CH2:34][CH3:35])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

8

Edukt 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86632921HCID 86632921, Verbindung

Produkt 1

HCID 86632922HCID 86632922, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (2-{7-amino-2-[(2,4-dichlorophenyl) (hydroxy)methyl]-1H-benzimidazol-1-yl}ethyl)carbamate (5.00 g, 11.1 mmol) in methanol (110 mL) and acetic acid (5.5 mL) was added acetoaldehyde (4.15 mL, 66.6 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (14.1 g, 66.5 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 3 h, the mixture was diluted with aqueous sodium hydrogen carbonate and 8N aqueous sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give a colorless solid (4.15 mg, 8.18 mmol, 74%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-31765e9c856a41ef94bf87c767e135bb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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