Potassium Iodide → (2R, 5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-N-methyl-benzenesulfonamide

HRID 480202노트

반응식

HRID 480202 반응식
Cl[CH2:2][C:3]([N:5]1[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][C@H:6]1[CH3:20])=[O:4].[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([OH:33])=[C:26]([S:28]([NH:31][CH3:32])(=[O:30])=[O:29])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC.C(OCC)(=O)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:33][CH2:2][C:3]([N:5]2[CH2:10][C@H:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:7][C@H:6]2[CH3:20])=[O:4])=[C:26]([S:28]([NH:31][CH3:32])(=[O:29])=[O:30])[CH:27]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 113584612-Chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneHCID 187681025-Chloro-2-hydroxy-N-methyl-benzenesulfonamide

생성물 1

HCID 59111303(2R, 5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-N-methyl-benzenesulfonamide수율 53%

시약·촉매·용매 2

HCID 6569Methyl Ethyl Ketone용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2R, 5S)-2-Chloro-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (375 mg, 1.26 mmol) in butanone (12 ml) was added 5-Chloro-2-hydroxy-N-methyl-benzenesulfonamide (280 mg, 1.26 mmol), potassium carbonate (348 mg, 2.52 mmol) and potassium iodide (209 mg, 1.26 mmol). The resulting reaction mixture was refluxed for 4 hours. It was allowed to cool, diluted with ethyl acetate and washed with brine. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the above titled compound (320 mg, 53% yield).

후처리

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 4 hours
  3. temperatureto cool
  4. washwashed with brine
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b94ae8813efb4a7abd959af2e8abea53
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649611B2

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