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

HRID 425378Notes

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-ace1d34bdb6845a0a6ef512c8503a229
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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