Sodium Bicarbonate → HCID 66974757, compound

HRID 2090780Notes

Reaction equation

HRID 2090780 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([S:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:12]=[C:11]([CH2:23][N:24](C)[C:25](=O)[O:26][C:27]([CH3:30])(C)C)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[C:33]([O:36]CC)(=[O:35])[CH3:34].Cl.C(=O)([O-])[OH:41].[Na+]>C(OCC)(=O)C>[C:27]([OH:26])(=[O:41])/[CH:30]=[CH:34]/[C:33]([OH:36])=[O:35].[CH3:25][NH:24][CH2:23][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:13]([S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974708HCID 66974708, compound

Product 1

HCID 66974757HCID 66974757, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution (2 mL) of tert-butyl {[5-(4-cyanophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (382 mg) in ethyl acetate was added a 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) at room temperature. The mixture was stirred for 3 hr, and basified with a saturated aqueous sodium hydrogencarbonate solution. 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 basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:9) to give a free salt of the title compound as a pale-yellow oil. The obtained free salt was dissolved in ethyl acetate, and added to a solution (2 mL) of fumaric acid (77.1 mg) in methanol. The solvent was evaporated under reduced pressure, and the residue was recrystallized from a mixed solvent of ethanol and water to give the title compound as colorless crystals (yield 218 mg, 55%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:9)

Sources & evidence

ORD record
ord-fc1fef2552024b7a95efe5478f42d85f
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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