Trifluoroacetic acid → HCID 178487211, compound
Reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@H:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH2:26][CH2:25][N:24]2[C:35]([C@@H:37]2[CH2:40][C@H:39]([CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])[CH2:38]2)=[O:36])=[O:22])[CH:12]=[C:13]([F:19])[C:14]=1[Si:15]([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])O.[Na+]>>[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@H:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH2:26][CH2:25][N:24]2[C:35]([C@@H:37]2[CH2:40][C@H:39]([CH2:41][C:42]([OH:44])=[O:43])[CH2:38]2)=[O:36])=[O:22])[CH:12]=[C:13]([F:19])[C:14]=1[Si:15]([CH3:17])([CH3:18])[CH3:16]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Cooled TFA (2 mL) was added to tert-butyl 2-(cis-3-((R)-1-((3,5-difluoro-4-(trimethylsilyl)phenyl)carbamoyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclobutyl)acetate (130 mg, 0.22 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 min. The pH of the reaction mixture was adjusted to 6 with cooled aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (78 mg, 0.146 mmol, 65.9%) as a white solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-2ebf9a902f2e452184d178b17841b63b
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
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