Sodium periodate → HCID 66583085, compound

HRID 1972696Notes

Reaction equation

HRID 1972696 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][CH:13]2[CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][C@@H:28]2[CH3:33])=[CH:8][CH:7]=1)([OH:5])[CH3:4].I([O-])(=O)(=O)=[O:37].[Na+]>CCOC(C)=O.O.O.O=[Ru]=O>[CH3:33][C@@H:28]1[N:27]([CH2:26][C@H:13]2[CH2:14][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:20])[CH2:16][CH2:17][N:12]2[C:9]2[CH:8]=[CH:7][C:6]([C@@:3]([OH:5])([CH3:4])[C:2]([F:1])([F:34])[F:35])=[CH:11][CH:10]=2)[C:32](=[O:37])[CH2:31][O:30][CH2:29]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 56933046HCID 56933046, compound

Product 1

HCID 66583085HCID 66583085, compoundYield 24.5%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S)-1,1,1-trifluoro-2-(4-(2-(((R)-3-methylmorpholino)methyl)-4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)propan-2-ol (50 mg, 0.094 mmol, Example 45, peak 2) in EtOAc (1 mL) was added to a mixture of dioxoruthenium hydrate (1.42 mg, 9.37 μmol, Sigma Aldrich, St. Louis, Mo.) and 10% aqueous sodium periodate (30.1 mg, 0.141 mmol, Sigma Aldrich, St. Louis, Mo.) in water (1.5 mL). The solution was stirred vigorously for 48 hours at room temperature. The reaction mixture was then concentrated in a GeneVac HT-12 (GeneVac Technologies, IPS Technologies, UK), re-dissolved in MeOH (1.5 mL), filtered through syringe filters (Pall Life Sciences, Acrodic®, 25 mm Syringe Filter w/0.45 μm HT Tuffryn® Membrane) and purified on Prep HPLC (Method: 10 min, 10 to 90% ACN, Water, 0.1% TFA, 254 nm; Column: Phenomenex, Gemini-NX, 5μ, C18, 150×30.00 mm) to afford (S)-5-methyl-4-(((S)-4-(thiophen-2-ylsulfonyl)-1-(4-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl)morpholin-3-one (12.6 mg).

Workup

  1. concentrationThe reaction mixture was then concentrated in a GeneVac HT-12 (GeneVac Technologies, IPS Technologies, UK)
  2. dissolutionre-dissolved in MeOH (1.5 mL)
  3. filtrationfiltered through syringe
  4. filtrationfilters (Pall Life Sciences, Acrodic®, 25 mm Syringe Filter w/0.45 μm HT Tuffryn® Membrane)
  5. custompurified on Prep HPLC (Method: 10 min, 10 to 90% ACN, Water, 0.1% TFA, 254 nm; Column: Phenomenex, Gemini-NX, 5μ, C18, 150×30.00 mm)

Sources & evidence

ORD record
ord-6a48070c02d243aebffb40d738fb1600
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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