Trifluoroacetic acid → HCID 178442435, compound
Reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]([CH3:45])([CH2:43][CH3:44])[CH2:10][C:11]1[N:12]=[C:13]([CH:23]([NH:38][C:39]([O:41][CH3:42])=[O:40])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)=[CH:27][CH:26]=2)[N:14](C(OC(C)(C)C)=O)[CH:15]=1>>[CH3:42][O:41][C:39](=[O:40])[NH:38][CH:23]([C:13]1[NH:14][CH:15]=[C:11]([CH2:10][C:9]([CH3:45])([CH3:8])[CH2:43][CH3:44])[N:12]=1)[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=2)=[CH:29][CH:30]=1Participants
3
Procedure
Trifluoroacetic acid (1 mL) was added to neat tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methoxy carbonyl)amino]ethyl}-1H-imidazole-1-carboxylate. After stirring at ambient temperature for 1 h, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparatory plate chromatography eluting with 100% ethyl acetate afforded the title compound. (M+H) found: 425.
Workup
- concentrationthe reaction mixture was concentrated in vacuo
- customThe residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide
- extractionThe aqueous phase was extracted with ethyl acetate
- dry with materialThe combined organic extracts were dried (magnesium sulfate)
- concentrationconcentrated in vacuo
- washPreparatory plate chromatography eluting with 100% ethyl acetate
Sources & evidence
- ORD record
- ord-0540344fd58d45afaf00c2642bdfa8c4
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318767B2
Reaction notes
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