Water → HCID 68000370, compound

HRID 1048570Notes

Reaction equation

HRID 1048570 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]([CH2:33][CH3:34])[CH2:26][NH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[C:5]1=[O:35])C=C.CC#N.O.I([O-])(=O)(=O)=O.[Na+].CC[O:49][C:50]([CH3:52])=[O:51]>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]([CH2:33][CH3:34])[CH2:26][NH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[C:5](=[O:35])[C@:4]([CH2:52][C:50]([OH:49])=[O:51])([CH3:1])[CH2:9]2)[CH:15]=[C:14]([F:16])[CH:13]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 67999017HCID 67999017, compound

Product 1

HCID 68000370HCID 68000370, compound

Reagents, catalysts & solvents 1

HCID 6093376Ruthenium trichloride hydrateCatalyst

Procedure

To a solution of N—((S)-2-((3S,5R,6S)-3-allyl-5-(3-chloro-5-fluorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butyl)ethanesulfonamide (Example 393, Step C, 120 mg, 0.216 mmol) in EtOAc:MeCN:water (1.450 mL) (2/2/3) at rt was added sodium periodate (185 mg, 0.864 mmol) slowly. Then ruthenium chloride hydrate (1.071 mg, 4.75 μmol) was added. The mixture was stirred vigourously at rt for 2 h. Then the mixture was filtered and the solid was washed with EtOAc. The filtrate was extracted with EtOAc 2×. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase preparatory HPLC (column: Gemini™ Prep C18 5 um column; Phenomenex, Torrance, Calif.; eluent: 0 to 100% MeCN+0.1% TFA in water+0.1% TFA, over 20 minutes) to give the title compound.

Workup

  1. filtrationThen the mixture was filtered
  2. washthe solid was washed with EtOAc
  3. extractionThe filtrate was extracted with EtOAc 2×
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by reverse phase preparatory HPLC (column: Gemini™ Prep C18 5 um column; Phenomenex, Torrance, Calif.; eluent: 0 to 100% MeCN+0.1% TFA in water+0.1% TFA, over 20 minutes)

Sources & evidence

ORD record
ord-7fa965961ac74c949dd92f248ca693cd
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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