Acetic Acid → HCID 68772648, Verbindung

HRID 1398926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398926
[NH2:1][C:2]1[C:7]2[N:8]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[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.[C:27](O)(=O)[CH3:28].[CH:31](=O)[CH3:32].C(O[BH3-])(=O)C.[Na+]>CO>[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][C:23]([O:25][CH3:26])=[O:24])[C:7]2[C:2]([N:1]([CH2:27][CH3:28])[CH2:31][CH3:32])=[CH:3][CH:4]=[CH:5][C:6]=2[N:10]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 68773584HCID 68773584, Verbindung

Produkt 1

HCID 68772648HCID 68772648, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of methyl 3-{7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-yl}propanoate (6.00 g, 14.7 mmol) and acetic acid (7.4 mL) in methanol (147 mL) was added acetaldehyde (4.95 mL, 88.2 mmol) at 0° C. After 30 min, sodium acetoxyborohydride (18.7 g, 88.2 mmol) was added. After 2 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous (6.30 g, 13.6 mmol, 92%).

Aufarbeitung

  1. waitAfter 2 h
  2. customthe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous sodium hydroxide (1 M) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-a6ee35376a1343e29923510a63ddcdb1
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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