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 932274Notes

Reaction equation

HRID 932274 reaction equation
[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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c70894b2c8644cc28cbd9bae138410d1
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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