Sodium Bisulfate → tert-Butyl {(1S)-1-methyl-2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 722982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722982
CON(C)[C:4](=[O:11])[C@@H:5]([NH:7][C:8](=[O:10])[O-:9])[CH3:6].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1.S([O-])(O)(=O)=O.[Na+]>O1CCCC1>[F:13][C:14]([F:24])([F:23])[C:15]1[CH:20]=[CH:19][C:18]([C:4](=[O:11])[C@@H:5]([NH:7][C:8](=[O:10])[O:9][C:15]([CH3:20])([CH3:16])[CH3:14])[CH3:6])=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 516919Sodium BisulfateHCID 86589062N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamateHCID 178506198HCID 178506198, Verbindung

Produkt 1

HCID 59339706tert-Butyl {(1S)-1-methyl-2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (9.6 g) in tetrahydrofuran (180 mL) was dropwise added at 0° C. to a solution of 1.48M 4-trifluoromethylphenylmagnesium bromide in tetrahydrofuran (70 mL) which had been prepared in another batch. The mixture was stirred at room temperature for 14 hours, and cooled down to 0° C. After addition of aqueous sodium hydrogen sulfate, the reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and filtered to remove the sodium sulfate. Evaporation of the organic solvent in vacuo gave t-butyl N-[(1S)-2-(4-trifluoromethylphenyl)-1-methyl-2-oxoethyl]carbamate (13.4 g) as an orange solid.

Aufarbeitung

  1. customhad been prepared in another batch
  2. temperaturecooled down to 0° C
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto remove the sodium sulfate
  8. customEvaporation of the organic solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-953c217b190e4a79a6adbcb9d7e83bb2
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138525B2

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