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

HRID 1354542노트

반응식

HRID 1354542 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-9432fc51f56046d6bfa110b3b97c0926
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223859B2

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