Water → 1-[6-(5-{2-cyclopentyl-1-[5-(methylsulfonyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882099Notes

Reaction equation

HRID 1882099 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:30])[CH2:28][OH:29])=[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[CH2:32]1.O.O[O:38][S:39]([O-:41])=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:30])[CH2:28][OH:29])=[CH:23][CH:22]=3)=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:39]([CH3:32])(=[O:41])=[O:38])=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593313131-[6-(5-{2-cyclopentyl-1-[5-(methylsulfanyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

Product 1

HCID 593313041-[6-(5-{2-cyclopentyl-1-[5-(methylsulfonyl)pyridin-2-yl]ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolYield 43%

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]ethane-1,2-diol (124 mg), tetrahydrofuran (2 mL), water (2 mL) and methanol (2 mL) was added Oxone (registered trademark) (216 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 (57.1 mg, yield 43%) 15 was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (99:1, volume ratio). MS: 456 (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-50e4006e93a641d98d91c6f5dd872352
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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