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 932275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 932275
[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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70573a14dc274b21804b987873ffb35f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296736B2

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