Water → (2R)-2-methylamino-3-phenyl-N-(2,2,2-trifluoroethyl)propionamide

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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

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-4b399d60fb0e47dda82a80b090281a91
Quelldatensatz: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06555570B2

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