Water → HCID 59331381, compound

HRID 1882097Notes

Reaction equation

HRID 1882097 reaction equation
[CH:1]1([CH2:6][CH:7]([C:16]2[NH:20][C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11](SC)=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCC[CH2:31]1.O.O[O:37][S:38]([O-:40])=O.[K+]>C(OCC)(=O)C.CO>[CH:1]1([CH2:6][CH:7]([C:16]2[NH:20][C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:38]([CH3:31])(=[O:40])=[O:37])=[CH:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59331572HCID 59331572, compound

Product 1

HCID 59331381HCID 59331381, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[6-(5-{2-cyclopentyl-1-[5-(methylsulfanyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethanol (313 mg), tetrahydrofuran (5.5 mL), water (5.5 mL) and methanol (5.5 mL) was added Oxone (registered trademark) (566 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (128 mg, yield 38%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 440 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-240f412a663f4d6580ec272f8669e44b
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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