Acetaldehyde → HCID 68761561, Verbindung

HRID 1628401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628401
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:27](=O)[CH3:28].[C:30](O[BH3-])(=O)[CH3:31].[Na+]>CO.C(O)(=O)C.C(=O)([O-])O.[Na+]>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:9]1[N:8]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:30][CH3:31])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

7

Edukt 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68763200HCID 68763200, Verbindung

Produkt 1

HCID 68761561HCID 68761561, VerbindungAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}propanoate (Reference Example 27; 214 mg, 0.544 mmol) in methanol (5.5 mL) and acetic acid (0.110 mL) was added acetaldehyde (0.204 mL, 3.27 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (692 mg, 3.27 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 12 hr, the mixture was diluted with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH-silica gel eluting with ethyl acetate to give the title compound as a solid (255 mg, 0.567 mmol, quant).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on NH-silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bf4a5e9f2b4c44728f65700bf8e10de9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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