Dimethyl Sulfide → ((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

HRID 932274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 932274
[O:1]=[O+][O-].[CH3:4][S:5]([O:8][CH2:9][C@:10]1([CH2:43][CH:44]=C)[CH2:15][C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C@@H:13]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:12]([C@@H:30]([CH2:40][CH3:41])[CH2:31][N:32]([CH3:39])[S:33]([CH:36]2[CH2:38][CH2:37]2)(=[O:35])=[O:34])[C:11]1=[O:42])(=[O:7])=[O:6].CSC>CO.C(Cl)Cl>[CH3:4][S:5]([O:8][CH2:9][C@:10]1([CH2:43][CH:44]=[O:1])[CH2:15][C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C@@H:13]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[N:12]([C@@H:30]([CH2:40][CH3:41])[CH2:31][N:32]([CH3:39])[S:33]([CH:36]2[CH2:37][CH2:38]2)(=[O:35])=[O:34])[C:11]1=[O:42])(=[O:7])=[O:6]

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 58573447((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate

Produkt 1

HCID 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Ozone was bubbled through a solution of ((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate (Example 414, Step E, 1.12 g, 1.703 mmol) in 10% MeOH-DCM at −78° C. until a blue color developed. The reaction was purged with nitrogen gas followed by addition of dimethyl sulfide (1.251 ml, 17.03 mmol). The reaction was warmed to room temperature. The crude material was purified by chromatography on 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. customThe reaction was purged with nitrogen gas
  2. customThe crude material was purified by chromatography on a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g)
  3. washeluting with a gradient of 0% to 80% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-c70894b2c8644cc28cbd9bae138410d1
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296736B2

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