p-Toluenesulfonic acid → [3-(4-Methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-carbamic acid benzyl ester
Reaktionsgleichung
[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14][C:15](=O)[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=1[NH2:25])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:12][CH2:13][CH2:14][C:15]1[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:18]=2[N:25]=1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
To a mixture of crude [3-(2-amino-3-methoxy-phenylcarbamoyl)-propyl]methyl-carbamic acid benzyl ester acid in 7 mL toluene were added a few drops of DMF and 523 mg of TsOH and the reaction mixture was heated at 150° C. for 2.5 h in the microwave. Sat. aq. NaHCO3 solution was added, the phases were separated and the organic phase was washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo. Purification by CC EtOAc/MeOH (10:1) yielded 0.74 g of the desired compound as brown foam.
Aufarbeitung
- customthe phases were separated
- washthe organic phase was washed with brine
- dry with materialThe combined organic phases were dried over MgSO4
- concentrationconcentrated in vacuo
- customPurification by CC EtOAc/MeOH (10:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-11d60e0e76f24498ab0e327f25c9b9ab
- Quelldatensatz
- uspto-grants-2012_11
- Patentnummer
- US08314253B2
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