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Acetaldehyde → Methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoate

HRID 1398805
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1398805
[NH2:1][C:2]1[C:7]2[N:8]([CH2:20][CH:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[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:28](=O)[CH3:29].[C:31](O[BH3-])(=O)[CH3:32].[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][CH:21]([OH:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:28][CH3:29])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1
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Komponenten

7

Edukt 3

HCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68762018Methyl 4-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}-3-hydroxybutanoate

Produkt 1

HCID 68765145Methyl 4-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-3-hydroxybutanoateAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a suspension of methyl 4-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}-3-hydroxybutanoate (Reference Example 82; 760 mg, 1.85 mmol) in methanol (19 mL) and acetic acid (0.380 mL) was added acetaldehyde (0.692 mL, 11.1 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (2.35 g, 11.1 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 15 hr, the mixture was diluted with aqueous 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 silica gel eluting with ethyl acetate to give the title compound as a solid (838 mg, 1.80 mmol, 97%).

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 silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c9fccffcf23f4eba800c10fba4e550d3
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901141B2

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