Ammonium Acetate → benzyl {2-(4-bromophenyl)-1-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate

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Reaktionsgleichung

C([O-])(=O)C.[NH4+:5].[Br:6][C:7]1[CH:37]=[CH:36][C:10]([CH2:11][CH:12]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]([NH:15][CH2:16][C:17](=O)[CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][CH3:21])=O)=[CH:9][CH:8]=1>C1(C)C(C)=CC=CC=1>[Br:6][C:7]1[CH:37]=[CH:36][C:10]([CH2:11][CH:12]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:13]2[NH:15][CH:16]=[C:17]([CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][CH3:21])[N:5]=2)=[CH:9][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

Ammonium acetate (48 g, 620 mmol) was added to an ambient temperature solution of benzyl {1-(4-bromobenzyl)-2-[(4,4-dimethyl-2-oxohexyl)amino]-2-oxoethyl}carbamate (6.23 g, 12.4 mmol) in xylene (124 mL). After stirring at 150° C. for 2 h, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford benzyl {2-(4-bromophenyl)-1-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate which was used in the subsequent step without further purification.

Aufarbeitung

customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
extractionextracted with methylene chloride
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-4c2a1a5ad6f64c93952bcdc57962a7d2
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08318767B2

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