Hydrochloric Acid → HCID 66939301, compound

HRID 1257461Notes

Reaction equation

HRID 1257461 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:18]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+].Cl>C(O)C.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[N:18]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66939745HCID 66939745, compound

Product 1

HCID 66939301HCID 66939301, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (4 mL) of the compound (540 mg, 1.3 mmol) obtained in Example 189d in ethanol was added 2N aqueous sodium hydroxide solution (2.6 mL, 5.3 mmol), 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 recrystallization (ethyl acetate-hexane) to give the title compound (380 mg, 76%) 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 recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c9befcfb6c7e4f178b34206297ed077d
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…