Ethyl Acetate → HCID 18785142, Verbindung

HRID 2295055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295055
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([F:21])=[CH:14][C:15]([N+:18]([O-])=O)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:18][C:15]1[CH:14]=[C:13]([F:21])[C:12]2[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH:9]=[N:10][C:11]=2[C:16]=1[CH3:17]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 21472716HCID 21472716, Verbindung

Produkt 1

HCID 18785142HCID 18785142, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonyl-7-fluoro-4-methyl-5-nitrobenzimidazole (0.776 g) in methanol (100 mL)/ethyl acetate (50 mL) is added palladium-on-carbon (10%, 0.1 g) and ammonium formate (0.663 g). The mixture is stirred at room temperature for 5 hours, then filtered on Celite, with methanol wash of the solids. The filtrate is rotary evaporated and the residue partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 25% ethyl acetate/hexane to afford 5-amino-1-tert-butoxycarbonyl-7-fluoro-4-methylbenzimidazole as a yellow oil.

Aufarbeitung

  1. filtrationfiltered on Celite, with methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe residue is purified by flash chromatography on silica gel
  8. washeluting with 25% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4e015f5151924f589b030f724309809e
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691370

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