Water → (2R)-2-methylamino-3-phenyl-N-(2,2,2-trifluoroethyl)propionamide
Reaktionsgleichung
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:16](=[O:23])[NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].O>ClCCl>[CH3:6][NH:7][C@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[O:23]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
N-Methyl-N-((1R)-2-phenyl-1-((2,2,2-trifluoroethyl)carbamoyl)ethyl)carbamic acid tert-butyl ester (3.45 g(9.57 mmol) was dissolved in dichloromethane (8 ml). The solution was cooled to 0° C. Trifluoroacetic acid (8 ml) was added. The reaction mixture was stirred for 45 min at 0° C. A saturated aqueous solution of sodium hydrogen carbonate (40 ml) was added. Solid sodium hydrogen carbonate was added until pH 7. Water (100 ml) was added, until a clear solution was obtained. The phases were separated. The aqueous phase was extracted with dichloromethane (3×30 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (180 g), using dichloromethane/methanol/25% aqueous ammonia as eluent to give 1.13 g of (2R)-2-methylamino-3-phenyl-N-(2,2,2-trifluoroethyl)propionamide.
Aufarbeitung
- customwas obtained
- customThe phases were separated
- extractionThe aqueous phase was extracted with dichloromethane (3×30 ml)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customThe solvent was removed in vacuo
- customThe crude product was purified by flash chromatography on silica (180 g)
Quellen und Nachweise
- ORD-Eintrag
- ord-1e84926b41b343f2a1a25c4cd531a9c3
- Quelldatensatz
- uspto-grants-1999_11
- Patentnummer
- US05977178
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