Acetic Acid → Methyl 2-((tert-butoxycarbonyl(methyl)amino)methyl)-1H-benzo[d]imidazole-4-carboxylate

HRID 1517381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517381
C(O)(=O)C.[NH2:5][C:6]1[C:15]([NH:16][C:17](=O)[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:20])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C1(C)C(C)=CC=CC=1>[C:24]([O:23][C:21]([N:19]([CH2:18][C:17]1[NH:16][C:15]2[CH:14]=[CH:13][CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]=2[N:5]=1)[CH3:20])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 58101623Methyl 2-amino-3-(2-(tert-butoxycarbonyl(methyl)amino)acetamido)benzoate

Produkt 1

HCID 58101688Methyl 2-((tert-butoxycarbonyl(methyl)amino)methyl)-1H-benzo[d]imidazole-4-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

Acetic acid (45 ml) was added to a solution of methyl 2-amino-3-(2-(tert-butoxycarbonyl(methyl)amino)acetamido)benzoate (19.28 mmol, 1.0 eq.) in xylene (130 ml) and the reaction mixture was heated under reflux for 1 h. When the reaction was complete (checking by TLC), the solvent was evaporated to dryness, the residue was dissolved in ethyl acetate and the solution was washed with water and NaCl solution. The organic phase was concentrated to dryness in vacuo in order to obtain the desired product, which was employed in the next stage without further purification. Yield: 90%

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. customthe solvent was evaporated to dryness
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water and NaCl solution
  6. concentrationThe organic phase was concentrated to dryness in vacuo in order

Quellen und Nachweise

ORD-Eintrag
ord-05311a0fb45a47a68c0875d33fe5e759
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232288B2

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