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Water → (2R,4S)-4-Acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl Ester

HRID 906217
ノート
印刷プレビュー

反応式

HRID 906217 の反応式
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C@@H:9]([O:11]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][N:7]1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[O:5])[CH3:2].[C:32]([O-])(=[O:34])[CH3:33].[K+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([O:11][C:32](=[O:34])[CH3:33])[CH2:8][N:7]1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:23])=[O:24])=[O:5])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 517044Potassium AcetateHCID 14541195(2R,4R)-1-(Toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic Acid Ethyl Ester

生成物 1

HCID 15629284(2R,4S)-4-Acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl Ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid ethyl ester (2) (1 g, 2.14 mmol) in dry DMF (25 mL) is added potassium acetate (0.314 g, 3.21 mmol) in one portion. The reaction mixture is then heated at 60° C. for 4 h. Water (50 mL) is added to the reaction mixture and extracted with ethyl acetate (2×75 mL), combined organic layer are washed with water (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to give the crude compound. Crude compound is purified by column chromatography over silica gel (100-200 mesh) using 15% ethyl acetate-hexane as eluent to give compound (3).

後処理

  1. extractionextracted with ethyl acetate (2×75 mL)
  2. washare washed with water (2×50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude compound
  7. customCrude compound is purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-9e2f7a1d3fd6492999db3178fcc2497d
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012983B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート