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 932274ノート

反応式

HRID 932274 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c70894b2c8644cc28cbd9bae138410d1
出典データセット
uspto-grants-2016_03
特許番号
US09296736B2

反応ノート

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