Water → HCID 59331302, compound

HRID 1882096Notes

Reaction equation

HRID 1882096 reaction equation
CS[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:17]2[NH:21][C:20]([C:22]3[N:27]=[CH:26][C:25]([CH:28]([OH:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:19][CH:18]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:7][CH:8]=1.O1CCC[CH2:32]1.O.O[O:38][S:39]([O-:41])=O.[K+]>C(OCC)(=O)C.CO>[CH3:32][S:39]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:17]2[NH:21][C:20]([C:22]3[N:27]=[CH:26][C:25]([CH:28]([OH:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:19][CH:18]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:7][CH:8]=1)(=[O:41])=[O:38]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 59331226HCID 59331226, compound

Product 1

HCID 59331302HCID 59331302, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[6-(5-{1-[5-(methylsulfanyl)pyridin-2-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethanol (76.1 mg), tetrahydrofuran (1 mL), water (1 mL) and methanol (1 mL) was added Oxone (registered trademark) (133 mg), and the mixture was stirred at room temperature for 4 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 (40.3 mg, yield 49%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (19:1, 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-3a44bd8e3dc14081ab630e5195334e8c
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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