Trifluoroacetic acid → HCID 136388334, compound

HRID 1861905Notes

Reaction equation

HRID 1861905 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:21])=[N:17][N+:18]([O-:20])=[O:19])[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N+:18]([N:17]=[C:16]([NH2:21])[NH:15][C:11]1[CH:10]=[C:9]([CH2:8][NH2:7])[CH:14]=[CH:13][CH:12]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136388335HCID 136388335, compound

Product 1

HCID 136388334HCID 136388334, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the compound (230 mg) obtained in Example 33, methylene chloride (3 ml) and trifluoroacetic acid (1.15 ml) was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure and 25% aqueous ammonia solution was added to the resulting residue, and the reaction mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; methanol) to give 117 mg of the titled compound (yield, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 25% aqueous ammonia solution
  2. additionwas added to the resulting residue
  3. extractionthe reaction mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; methanol)

Sources & evidence

ORD record
ord-50674ecde2664803a2aa2703fd0eddbb
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

Loading…