Ethyl Acetate → HCID 67397600, compound

HRID 1426722Notes

Reaction equation

HRID 1426722 reaction equation
[F:1][C:2]1[C:3]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:4][N:5]([S:14](C2C=CC=C(CSC)C=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.Cl[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([C:43](OO)=O)[CH:38]=1.[S:47]([O-:51])([O-])(=[O:49])=S.[Na+].[Na+].[C:54](OCC)(=O)C>>[F:1][C:2]1[C:3]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[CH:4][N:5]([S:14]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43][S:47]([CH3:54])(=[O:51])=[O:49])[CH:38]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 8857Ethyl Acetate2×HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 67395914HCID 67395914, compound

Product 1

HCID 67397600HCID 67397600, compoundYield 92%

Procedure

To a solution of tert-butyl {[4-fluoro-5-(2-fluoropyridin-3-yl)-1-({3-[(methylthio)methyl]phenyl}sulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (235 mg) in ethyl acetate (3 mL) was added dropwise a solution of 3-chloroperbenzoic acid (620 mg) in ethyl acetate (2 mL) under ice-cooling, and the mixture was stirred for 2 hr. Saturated aqueous sodium thiosulfate solution was added, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with saturated aqueous sodium hydrogen carbonate solution. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as a pale-yellow oil (yield 231 mg, 92%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe separated organic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3)

Sources & evidence

ORD record
ord-1b19977cd01647cdbfe3e8e650f125f3
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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