Hydrochloric Acid → HCID 86650589, compound

HRID 1257347Notes

Reaction equation

HRID 1257347 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([O:26]CC)=[O:25])[CH:21]=[N:20]3)[S:16][CH:17]=2)[N:4]=1.[OH-].[Na+].Cl>C(O)C.[Cl-].[Na+].O>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([C:13]2[N:14]=[C:15]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[N:20]3)[S:16][CH:17]=2)[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86650590HCID 86650590, compound

Product 1

HCID 86650589HCID 86650589, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The crude compound (100 mg) obtained in Example 33d was dissolved in ethanol (2 mL), 2N aqueous sodium hydroxide solution (0.44 mL, 0.88 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with 1N aqueous hydrochloric acid solution, saturated brine was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by preparative high performance liquid chromatography and then recrystallization (ethyl acetate-hexane) to give the title compound (6 mg, 7% in 2 steps) as colorless crystals.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by preparative high performance liquid chromatography
  8. customrecrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-82ece652c36340ba970afbe811f68d1f
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…