Tetrahydrofuran → HCID 59331486, compound

HRID 1882049Notes

Reaction equation

HRID 1882049 reaction equation
CS[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:17]2[NH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:20][CH:21]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][N:4]=1.O1CCC[CH2:29]1.O[O:34][S:35]([O-:37])=O.[K+].C(=O)([O-])O.[Na+]>O.CO>[CH3:29][S:35]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:17]2[NH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:20][CH:21]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][N:4]=1)(=[O:37])=[O:34]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59331268HCID 59331268, compound

Product 1

HCID 59331486HCID 59331486, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(methylsulfanyl)-5-[1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]pyridine (0.365 g) in a mixed solvent of tetrahydrofuran (10 mL), methanol (5 mL) and water (5 mL) was added Oxone (registered trade mark, 1.77 g), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio) and recrystallized from hexane-ethyl acetate to give the title compound (0.200 g, yield 51%) as colorless crystals. MS: 412 (MH+). melting point 89-90° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-e71e03d4ddc547389e9b8b15888f2203
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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