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

HRID 1354543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354543
O1CCCC1.[F:6][C:7]([F:27])([F:26])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:25])[CH2:16][C@@H:17](OS(C)(=O)=O)[CH2:18][CH3:19])=[CH:10][CH:9]=1.O1CCCC1.C([Mg]Cl)(C)(C)C>O>[CH2:18]([C@H:17]1[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([F:27])([F:26])[F:6])=[CH:9][CH:10]=2)[C:15](=[O:25])[CH2:16]1)[CH3:19]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 11961983(S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amideHCID 178420653HCID 178420653, Verbindung

Produkt 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran solution (1 mL) containing 200 mg (0.589 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide produced in Example 3, 368.4 mg (0.589 mmol) of tert-butylmagnesium chloride tetrahydrofuran solution (1.6 mmol/g) was added dropwise at room temperature for 5 minutes. After stirring at room temperature for further 2 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 (136.4 mg). The reaction yield of the product was determined by the method described in Example 7 to be 61%.

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-9220852978ce4a5ba6841191d5997032
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223859B2

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