Water → (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone

HRID 1354544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354544
[H-].[Na+].[F:3][C:4]([F:30])([F:29])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[CH2:13][C@@H:14](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH3:16])=[CH:7][CH:6]=1.O>O1CCCC1>[CH2:15]([C@H:14]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([F:30])([F:29])[F:3])=[CH:6][CH:7]=2)[C:12](=[O:28])[CH2:13]1)[CH3:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86594547(S)-N-[4-(trifluoromethyl)phenyl]-3-(4-methylphenyl)sulfonyloxypentanoic acid amide

Produkt 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneAusbeute 109,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

26.5 mg of sodium hydride (60 wt %; 0.662 mmol) was suspended in tetrahydrofuran (1.5 mL) and to the solution, a tetrahydrofuran solution (1.5 mL) containing 274.9 mg (0.662 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-(4-methylphenyl)sulfonyloxypentanoic acid amide produced in Example 4 was added dropwise at room temperature for 5 minutes. After stirring at room temperature for further 3.5 hours, water (5 mL) was added and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone as a brown solid (176.1 mg). The reaction yield of the product was determined by the method described in Example 7 to be 83%.

Aufarbeitung

  1. additionwas added dropwise at room temperature for 5 minutes
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialthe product was dried with anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-17c08339bc184fca91a2d9565557332e
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223859B2

Notizen zur Reaktion

Wird geladen…