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

HRID 906217
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HRID 906217 반응식
[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]
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HCID 962WaterHCID 517044Potassium AcetateHCID 14541195(2R,4R)-1-(Toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic Acid Ethyl Ester

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e2f7a1d3fd6492999db3178fcc2497d
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012983B2

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