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

HRID 1881459Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-4c2a1a5ad6f64c93952bcdc57962a7d2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318767B2

Reaction notes

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