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

HRID 1354541ノート

反応式

HRID 1354541 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-ff4afd4afe1c4b3c888029700dece646
出典データセット
uspto-grants-2007_05
特許番号
US07223859B2

反応ノート

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