Hydrochloric Acid → HCID 67400734, compound

HRID 1186307Notes

Reaction equation

HRID 1186307 reaction equation
[F:1][C:2]([F:31])([F:30])[CH:3]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[O:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]1[NH:15][S:16]([CH2:19][CH2:20][C:21]([O-:23])=[O:22])(=[O:18])=[O:17].[OH-].[Na+].Cl>CO>[F:31][C:2]([F:1])([F:30])[CH:3]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[O:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]1[NH:15][S:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86657927HCID 86657927, compound

Product 1

HCID 67400734HCID 67400734, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 295 (380 mg, 0.680 mmol) obtained in Example 289 was dissolved in methanol (3.00 mL). To this, a 2.00 mol/L aqueous sodium hydroxide solution (3.00 mL) was added and the mixture was stirred at room temperature for 1 hour. By addition of a 2.00 mol/L aqueous hydrochloric acid solution to neutralize the reaction mixture, the reaction was stopped. Then, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 14/1) to give Compound 296 (308 mg, yield: 37%).

Workup

  1. extractionThen, extraction with ethyl acetate
  2. washby washing with brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 14/1)

Sources & evidence

ORD record
ord-3becb7d5524a45c78bef11ec5e4f08cb
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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