Hydrochloric Acid → HCID 136159996, compound

HRID 1947224Notes

Reaction equation

HRID 1947224 reaction equation
Cl.[CH:2]([N:5]1[C:9]([S:10]([CH3:13])(=[O:12])=[O:11])=[N:8][N:7]=[C:6]1[C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23]COC)=[CH:16][C:15]=1[O:27]COC)([CH3:4])[CH3:3].C(=O)([O-])O.[Na+]>CO>[CH:20]([C:18]1[CH:19]=[C:14]([C:6]2[N:5]([CH:2]([CH3:4])[CH3:3])[C:9]([S:10]([CH3:13])(=[O:12])=[O:11])=[N:8][N:7]=2)[C:15]([OH:27])=[CH:16][C:17]=1[OH:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59829848HCID 59829848, compound

Product 1

HCID 136159996HCID 136159996, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 N hydrochloric acid (0.5 mL) was added to a methanol solution (0.5 mL) of 4-isopropyl-3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-5-methylsulfonyl-4H-[1,2,4]triazole (an intermediate of Example 2-13 F63-05: 35 mg, 82 μmol) and the mixture was stirred for 8 hours. After cooling to ice cold conditions, it was neutralized by adding saturated aqueous sodium hydrogencarbonate. The solution was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure. The solids thus obtained were dried under reduced pressure to obtain 4-isopropyl-6-(4-isopropyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)-benzene-1,3-diol (SFN-a21, white solids, 20.8 mg, 75%).

Workup

  1. temperatureAfter cooling to ice cold conditions, it
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customsodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe solids thus obtained
  8. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-0ea3c8da09954398ad7465e44f47c6ec
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

Loading…