Water → 2-methyl-1-[6-(5-{1-[5-(methylsulfonyl)pyridin-2-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]propane-1,2-diol

HRID 1882068Notes

Reaction equation

HRID 1882068 reaction equation
[CH3:1][C:2]([OH:33])([CH3:32])[CH:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[NH:12][C:13]([CH:16]([C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][N:25]=3)[CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:15]=2)=[CH:9][CH:10]=1)[OH:4].[OH2:34].C([O-])([O-])=O.C([O-])([O-])=O.[OH:43]O.OO.OO.[Na+].[Na+].[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH3:32][C:2]([OH:33])([CH3:1])[CH:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[NH:12][C:13]([CH:16]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:31])(=[O:43])=[O:34])=[CH:26][N:25]=3)[CH2:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:14][CH:15]=2)=[CH:9][CH:10]=1)[OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 159762Sodium percarbonate2×HCID 59331498HCID 59331498, compound

Product 1

HCID 593312272-methyl-1-[6-(5-{1-[5-(methylsulfonyl)pyridin-2-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]propane-1,2-diolYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-methyl-1-[6-(5-{1-[5-(methylsulfanyl)pyridin-2-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]propane-1,2-diol (0.37 g), water (4 mL) and acetonitrile (6 mL) was added sodium percarbonate (0.25 g), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added sodium percarbonate (0.10 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium sulfite solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (0.33 g, yield 84%) was obtained as a pale-yellow amorphous solid from a fraction eluted with tetrahydrofuran-hexane (4:1, volume ratio). MS: 500 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9fe9a83e06dd496ab0475cd9bcb5bd90
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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