Ethyl Acetate → 5-Amino-1-1-butoxycarbonyl-4-methylbenzimidazole

HRID 2260723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2260723
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-])=O)=[C:16]([CH3:17])[C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])(C)C.[C:21](OCC)(=O)[CH3:22].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:6]([O:5][CH2:1][CH2:4][CH2:21][CH3:22])=[O:7])[CH:9]=[N:10][C:11]=2[C:16]=1[CH3:17]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 158963171h-Benzimidazole-1-carboxylic acid,4-methyl-5-nitro-,1,1-dimethylethyl ester

Produkt 1

HCID 677887485-Amino-1-1-butoxycarbonyl-4-methylbenzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonyl-4-methyl-5-nitrobenzimidazole (8 g) in methanol (40 mL)/ethyl acetate (400 mL) is added palladium-on-carbon (Pd/C) (10%, 0.5 g) and ammonium formate (7.27g). The mixture is stirred at 50° C. for 2 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 washed with saturated ammonium chloride, dried over magnesium sulfate, filtered and rotary evaporated to afford pure 5-amino-1-1-butoxycarbonyl-4-methylbenzimidazole as an off-white solid.

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. washThe organic layer is washed with saturated ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customrotary evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bd7367dff5954afd98f94bebdb299711
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05478858

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