Sodium Hydroxide → HCID 67396538, compound

HRID 1426674Notes

Reaction equation

HRID 1426674 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:12](S(C3C=NC=CC=3)(=O)=O)[CH:11]=[C:10]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66974416HCID 66974416, compound

Product 1

HCID 67396538HCID 67396538, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl {[5-(2-fluoropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (4.78 g) was dissolved in tetrahydrofuran (20 mL) and methanol (10 mL), 8 mol/L aqueous sodium hydroxide solution (4 mL) was added under ice-cooling. After stirring at room temperature for 4 hr, about half of the solvent was evaporated under reduced pressure, water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→ethyl acetate) to give the title compound as a pale-yellow oil (yield 2.84 g, 87%).

Workup

  1. temperaturecooling
  2. customwas evaporated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→ethyl acetate)

Sources & evidence

ORD record
ord-b10470cfe8714e17bcbf1fdf24b2edba
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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