Methanol → HCID 58305762, compound

HRID 2280307Notes

Reaction equation

HRID 2280307 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:5]([CH3:29])[CH:4]=1)#[N:2].O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:32]([CH3:36])(=[O:34])=[O:31])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:5]([CH3:29])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 58305617HCID 58305617, compound

Product 1

HCID 58305762HCID 58305762, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a vigorously stirred solution of ethyl 3-(1-(4-cyano-2-methylphenyl)-5-(4-(methylthio)phenyl)-1H-pyrrol-2-yl)propanoate 28A (50 mg, 0.12 mmol) in methanol (1 mL) was added dropwise a solution of oxone (300 mg, 0.74 mmol) in water (5 mL) at 20° C. The mixture was stirred for 1 h, diluted with water (10 mL) and extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered, concentrated and purified by silica gel flash chromatography (PE:EA=3:1) to afford ethyl 3-(1-(4-cyano-2-methylphenyl)-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-2-yl)propanoate (28B) as a brown solid (120 mg, 37%).

Workup

  1. extractionextracted with ethyl acetate (30 mL×3)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel flash chromatography (PE:EA=3:1)

Sources & evidence

ORD record
ord-333840bcac2b4e1eb5a3cf190c7537b1
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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