Trifluoroacetic acid → HCID 54026226, compound

HRID 1417506Notes

Reaction equation

HRID 1417506 reaction equation
F[C:2](F)(F)[C:3](O)=O.[CH2:8]([N:15]1[C:27]2[C:26]([S:28]([CH3:30])=O)=[C:25]([CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH:24]=[C:23]([CH3:38])[C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([N:15]1[C:27]2[C:26]([S:28][CH2:30][CH2:2][CH3:3])=[C:25]([CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[CH:24]=[C:23]([CH3:38])[C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53951018HCID 53951018, compound

Product 1

HCID 54026226HCID 54026226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.1 ml of anhydrous trifluoroacetic acid was added to 5 ml of a solution of 100 mg isopropyl (9-benzyl-4-methyl-1-methylsulfinylcarbazol-2-yl)acetate, as obtained in Example 215, in methylene chloride, and the reaction mixture was refluxed for 30 minutes. The solvent was then removed by evaporation under reduced pressure and the residue was dissolved in 2 ml of methylene chloride. 0.5 ml of n-propyl iodide, 1 ml of triethylamine and 1 ml of methanol were then all added to the resulting solution at room temperature and the reaction mixture was stirred for 30 minutes. After this time, the reaction mixture was diluted with an excess of ethyl acetate, and washed with a dilute aqueous solution of hydrogen chloride, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, in that order. The resulting organic layer was dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 4-6% v/v solution of ethyl acetate in hexane) to yield 86 mg of the title compound as a solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. customThe solvent was then removed by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in 2 ml of methylene chloride
  4. additionall added to the resulting solution at room temperature
  5. additionAfter this time, the reaction mixture was diluted with an excess of ethyl acetate
  6. washwashed with a dilute aqueous solution of hydrogen chloride
  7. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-48fd5a8bf9294876adaf9af6e0f3c4fc
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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