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

HRID 1354542Notes

Reaction equation

HRID 1354542 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:28])([F:27])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[CH2:17][C@@H:18](OS(C)(=O)=O)[CH2:19][CH3:20])=[CH:11][CH:10]=1.O>O1CCCC1>[CH2:19]([C@H:18]1[N:15]([C:12]2[CH:13]=[CH:14][C:9]([C:8]([F:28])([F:27])[F:7])=[CH:10][CH:11]=2)[C:16](=[O:26])[CH2:17]1)[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 11961983(S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

99.2 mg (0.884 mmol) of potassium tert-butoxide was suspended in tetrahydrofuran (1.5 mL) and a tetrahydrofuran solution (1.5 mL) containing 300 mg (0.884 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide produced in Example 3 was added dropwise thereto at room temperature for 5 minutes. After stirring at room temperature for further 5.5 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 (194.0 mg). The reaction yield of the product was determined by the method described in Example 7 to be 81%.

Workup

  1. additionwas added dropwise
  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

Sources & evidence

ORD record
ord-9432fc51f56046d6bfa110b3b97c0926
Source dataset
uspto-grants-2007_05
Patent number
US07223859B2

Reaction notes

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