Ammonium Acetate → HCID 178502198, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH:15]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]([CH3:18])[CH3:17])[CH:10]([C:25](=O)[NH:26][CH2:27][C:28]([C:30]2[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:42]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH:15]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]([CH3:17])[CH3:18])[CH:10]([C:25]2[NH:26][CH:27]=[C:28]([C:30]3[CH:31]=[CH:32][C:33]([Br:36])=[CH:34][CH:35]=3)[N:42]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- 135 °C
Procedure
3-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-(2-methoxycarbonylamino-3-methyl-butyryl)-piperazine-1-carboxylic acid tert-butyl ester (2.0 g, 3.43 mmol) was dissolved in m-xylenes (18 mL) and heated at 135° C. Solid ammonium acetate (1.70 g, 22.0 mmol) was added and the reaction was stirred at 135° C. After 120 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude material was purified via silica gel chromatography (eluent: EtOAc w MeOH 10%/hexanes) to yield the product 3-[4-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-(2-methoxycarbonylamino-3-methyl-butyryl)-piperazine-1-carboxylic acid tert-butyl ester (674 mg, 1.19 mmol): LCMS-ESI+: calc'd for C25H34BrN5O5: 564.5 (M+). Found: 564.2/566.2 (M+H+).
Workup
- temperaturethe reaction was cooled to room temperature
- customthe volatiles were removed in vacuo
- customThe crude material was purified via silica gel chromatography (eluent: EtOAc w MeOH 10%/hexanes)
Sources & evidence
- ORD record
- ord-984952d63e324e82a99e7612660d5229
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822430B2
Reaction notes
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