Ammonium Acetate → HCID 178502207, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13](=O)[NH:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)=O)[N:10]([C:26](=[O:36])[CH:27]([NH:31][C:32]([O:34][CH3:35])=[O:33])[CH:28]([CH3:30])[CH3:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:41]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)[N:41]=2)[N:10]([C:26](=[O:36])[CH:27]([NH:31][C:32]([O:34][CH3:35])=[O:33])[CH:28]([CH3:30])[CH3:29])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
Conditions
- Temperature
- 135 °C
Procedure
4-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-3-(2-methoxycarbonylamino-3-methyl-butyryl)-imidazolidine-1-carboxylic acid tert-butyl ester (723 mg) was dissolved in m-xylenes (6.0 mL) and heated at 135° C. Solid ammonium acetate (500 mg, 6.48 mmol) was added and the reaction was stirred at 135° C. After 45 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 10% MeOH/hexanes) to yield the product 4-(4-Bromo-phenyl)-3′-(2-methoxycarbonylamino-3-methyl-butyryl)-2′,3′,4′,5′-tetrahydro-1H-[2,4′]biimidazolyl-1′-carboxylic acid tert-butyl ester (436 mg): LCMS-ESI+: calc'd for C24H32BrN5O5: 550.4 (M+). Found: 551.2/553.2 (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 10% MeOH/hexanes)
Sources & evidence
- ORD record
- ord-de2a081d82124ee4ab4190840313f062
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841278B2
Reaction notes
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