Dimethylformamide → (S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 469733

反応式

HRID 469733 の反応式
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.[Cl:19][C:20]1[C:21](F)=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>[Cl-].[NH4+]>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[C:21]1[C:20]([Cl:19])=[CH:25][C:24]([C:26]([F:29])([F:27])[F:28])=[CH:23][N:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridineHCID 10888648tert-Butyl 5-oxo-L-prolinate

生成物 1

HCID 67455590(S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 25517Ammonium Chloride溶媒

実験手順

To a stirred solution of (S)-5-oxo-pyrrolidine-2-carboxylic acid tert-butyl ester (740 mg, 4 mmol) in N,N-dimethylformamide (5 mL) sodium hydride (180 mg of 60% dispersion in mineral oil, 4.5 mmol) is added at room temperature. After 10 minutes, 3-chloro-2-fluoro-5-trifluoromethylpyridine (1 mL, 8 mmol) is added and the suspension stirred at room temperature. After 3 h the reaction mixture is treated with saturated ammonium chloride solution (150 mL), extracted with dichloromethane (2×100 mL). Combined extracts washed with brine (2×50 mL), water, dried over anhydrous Na2SO4 and solvent removed in vacuo. The crude is purified by chromatography over silica gel eluting with hexanes/ethyl acetate to give the title compound, ESI m/z 365 [M+H]+.

後処理

  1. extractionextracted with dichloromethane (2×100 mL)
  2. washCombined extracts washed with brine (2×50 mL), water
  3. dry with materialdried over anhydrous Na2SO4 and solvent
  4. customremoved in vacuo
  5. customThe crude is purified by chromatography over silica gel eluting with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-43678106045c449a87c7dd4fb7cc0ff9
出典データセット
uspto-grants-2014_01
特許番号
US08629157B2

関連ノート

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