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

HRID 1354544ノート

反応式

HRID 1354544 の反応式
[H-].[Na+].[F:3][C:4]([F:30])([F:29])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[CH2:13][C@@H:14](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH3:16])=[CH:7][CH:6]=1.O>O1CCCC1>[CH2:15]([C@H:14]1[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([F:30])([F:29])[F:3])=[CH:6][CH:7]=2)[C:12](=[O:28])[CH2:13]1)[CH3:16]

参加物

5

反応物 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86594547(S)-N-[4-(trifluoromethyl)phenyl]-3-(4-methylphenyl)sulfonyloxypentanoic acid amide

生成物 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone収率 109.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

26.5 mg of sodium hydride (60 wt %; 0.662 mmol) was suspended in tetrahydrofuran (1.5 mL) and to the solution, a tetrahydrofuran solution (1.5 mL) containing 274.9 mg (0.662 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-(4-methylphenyl)sulfonyloxypentanoic acid amide produced in Example 4 was added dropwise 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 (176.1 mg). The reaction yield of the product was determined by the method described in Example 7 to be 83%.

後処理

  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

出典と根拠

ORDレコード
ord-17c08339bc184fca91a2d9565557332e
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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