Potassium Carbonate → (S)-tert-butyl 1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethylcarbamate

HRID 1506620

Reaktionsgleichung

Reaktionsgleichung von HRID 1506620
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 403081-(Bromomethyl)-2-methoxybenzeneHCID 57976325[(S)-1-(1H-imidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 90281194(S)-tert-butyl 1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To (S)-tert-butyl 1-(1H-imidazol-2-yl)-2-phenylethylcarbamate (120 mg, 0.42 mmol) in DMF (1 mL) was added 1-(bromomethyl)-2-methoxybenzene (58 μL, 0.42 mmol), K2CO3 (70 mg, 0.5 mmol) and TBAI (5 mg) and heated to 90° C. After stirring for 1 hr and cooling to ambient temperature, the reaction was partitioned between EtOAc and H2O. The organics were separated, washed with saturated aqueous NaHCO3, and saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product: MS (m/z) 408.2 [M+H]+.

Aufarbeitung

  1. temperaturecooling to ambient temperature
  2. customthe reaction was partitioned between EtOAc and H2O
  3. customThe organics were separated
  4. washwashed with saturated aqueous NaHCO3, and saturated aqueous NaCl
  5. customSolvents were removed in vacuo
  6. customthe residue purified by column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-a5fcf6e01eb2447f9ae137cffe635255
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09220710B2

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