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

HRID 1354543ノート

反応式

HRID 1354543 の反応式
O1CCCC1.[F:6][C:7]([F:27])([F:26])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:25])[CH2:16][C@@H:17](OS(C)(=O)=O)[CH2:18][CH3:19])=[CH:10][CH:9]=1.O1CCCC1.C([Mg]Cl)(C)(C)C>O>[CH2:18]([C@H:17]1[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([F:27])([F:26])[F:6])=[CH:9][CH:10]=2)[C:15](=[O:25])[CH2:16]1)[CH3:19]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 11961983(S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amideHCID 178420653HCID 178420653、化合物

生成物 1

HCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone収率 95.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 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, 368.4 mg (0.589 mmol) of tert-butylmagnesium chloride tetrahydrofuran solution (1.6 mmol/g) was added dropwise at room temperature for 5 minutes. After stirring at room temperature for further 2 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 (136.4 mg). The reaction yield of the product was determined by the method described in Example 7 to be 61%.

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-9220852978ce4a5ba6841191d5997032
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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