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

HRID 1354541노트

반응식

HRID 1354541 반응식
C[O-].[Na+].[F:4][C:5]([F:25])([F:24])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:23])[CH2:14][C@@H:15](OS(C)(=O)=O)[CH2:16][CH3:17])=[CH:8][CH:7]=1.O>O1CCCC1>[CH2:16]([C@H:15]1[N:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([F:25])([F:24])[F:4])=[CH:7][CH:8]=2)[C:13](=[O:23])[CH2:14]1)[CH3:17]

참가 물질

5

반응물 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 11961983(S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide

생성물 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone수율 98.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

31.8 mg (0.589 mmol) of sodium methoxide was suspended in tetrahydrofuran (1 mL) and 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 was added dropwise thereto 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 (141.6 mg). The reaction yield of the product was determined by HPLC analysis (column; NACALAI COSMO SEAL 5C18-AR packed column 4.6×250 mm: eluent; acetonitrile/5 mM phosphate buffer solution (pH=3)=1/1: flow rate; 1.0 mL/min: column temperature; 30° C: detector; UV 210 nm) to be 60%.

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-ff4afd4afe1c4b3c888029700dece646
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223859B2

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