Water → HCID 58573496, compound

HRID 1048573Notes

Reaction equation

HRID 1048573 reaction equation
[CH2:1]([C@@:4]1(C)[CH2:9][C@H:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[C@@H:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[N:6]([C@@H:25]([CH2:31][CH3:32])[CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:5]1=[O:33])C=C.O.I([O-])(=O)(=O)=O.[Na+].CC[O:44][C:45]([CH3:47])=[O:46]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[Cl:17][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[N:6]([C@@H:25]([CH2:31][CH3:32])[CH2:26][S:27]([CH3:30])(=[O:28])=[O:29])[C:5](=[O:33])[C@:4]([CH2:47][C:45]([OH:44])=[O:46])([CH3:1])[CH2:9]2)[CH:15]=[C:14]([F:16])[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 58573831HCID 58573831, compound

Product 1

HCID 58573496HCID 58573496, compound

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chloro-5-fluorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(methylsulfonyl)butan-2-yl)piperidin-2-one (Example 395, Step B, 58 mg, 0.110 mmol) in acetonitrile (1.0 mL), EtOAc (1.0 mL), and water (1.5 mL) was added ruthenium(III) chloride hydrate (0.55 mg, 2.42 μmol) and sodium periodate (144 mg, 0.672 mmol). After 2 hours, the mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by preparative thin layer chromatography on silica gel (eluent: 10% MeOH/DCM) to provide the title compound.

Workup

  1. customthe mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: 10% MeOH/DCM)

Sources & evidence

ORD record
ord-70db23d00b9944b6b0fb99396c002f0e
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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