Trifluoroacetic acid → HCID 178487604, Verbindung
Reaktionsgleichung
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@@H:23]2[N:32]([C:33]([C@@H:35]3[CH2:38][C@H:37]([CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[CH2:36]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:47][CH3:48])[CH:26]=[CH:25][C:24]2=3)=[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[N:32]([C:33]([C@@H:35]3[CH2:36][C@H:37]([CH2:39][C:40]([OH:42])=[O:41])[CH2:38]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:47][CH3:48])[CH:26]=[CH:25][C:24]2=3)=[O:22])[CH:12]=[C:13]([F:19])[C:14]=1[Si:15]([CH3:18])([CH3:17])[CH3:16]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Cooled TFA (2 mL) was added to tert-butyl 2-(cis-3-((R)-5-((3,5-difluoro-4-(trimethylsilyl)phenyl)carbamoyl)-2-methoxy-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclobutyl)acetate (100 mg, 0.17 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 (67.0 mg, 0.126 mmol, 74.1%) as a white solid.
Aufarbeitung
- 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)
Quellen und Nachweise
- ORD-Eintrag
- ord-02886f4ba65040309d1acad8ab8cfe8e
- Quelldatensatz
- uspto-grants-2016_06
- Patentnummer
- US09365520B2
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