Methanol → Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-3-(((methylsulfonyl)oxy)methyl)-2-oxopiperidin-3-yl)acetate

HRID 932275노트

반응식

HRID 932275 반응식
[CH3:1][S:2]([O:5][CH2:6][C@:7]1([CH2:40][CH:41]=[O:42])[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[C@@H:10]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:9]([C@@H:27]([CH2:37][CH3:38])[CH2:28][N:29]([CH3:36])[S:30]([CH:33]2[CH2:35][CH2:34]2)(=[O:32])=[O:31])[C:8]1=[O:39])(=[O:4])=[O:3].OOS([O-])=O.[K+].[CH3:49][OH:50]>C(Cl)Cl.O>[Cl:19][C:15]1[CH:14]=[C:13]([C@@H:11]2[C@@H:10]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[N:9]([C@@H:27]([CH2:37][CH3:38])[CH2:28][N:29]([CH3:36])[S:30]([CH:33]3[CH2:34][CH2:35]3)(=[O:32])=[O:31])[C:8](=[O:39])[C@:7]([CH2:40][C:41]([O:50][CH3:49])=[O:42])([CH2:6][O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12]2)[CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 58573120((3R,5R,6S)-5-(3-Chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxo-3-(2-oxoethyl)piperidin-3-yl)methyl methanesulfonate

생성물 1

HCID 58573826Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-3-(((methylsulfonyl)oxy)methyl)-2-oxopiperidin-3-yl)acetate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of ((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxo-3-(2-oxoethyl)piperidin-3-yl)methyl methanesulfonate (Example 414, Step F, 1.0 g, 1.516 mmol) in MeOH was treated with Oxone (0.932 g, 1.516 mmol) over a weekend. The reaction mixture was diluted with DCM and water. The organic extract was washed with satd NaCl and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a white solid. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g), eluting with a gradient of 0% to 80% EtOAc in hexane, to provide the title compound as an oil.

후처리

  1. extractionThe organic extract
  2. washwas washed with satd NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material as a white solid
  7. customThe product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g)
  8. washeluting with a gradient of 0% to 80% EtOAc in hexane

출처 및 근거

ORD 기록
ord-70573a14dc274b21804b987873ffb35f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296736B2

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