Trifluoroacetic acid → HCID 12043725, compound

HRID 1370553Notes

Reaction equation

HRID 1370553 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([N:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([N:24]4[CH2:29][CH2:28][N:27]([C:30](OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[CH:19][CH:20]=3)[C:15]2=[O:37])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+].[C:49]1([CH:55]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH2:56]CBr)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O>[CH:8]1([N:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][C:18]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][CH2:56][CH:55]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)[C:59]5[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=5)[CH2:26][CH2:25]4)=[CH:19][CH:20]=3)[C:15]2=[O:37])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 883331,1'-(3-Bromopropylidene)bisbenzeneHCID 516892Sodium BicarbonateHCID 18510913HCID 18510913, compound

Product 1

HCID 12043725HCID 12043725, compoundYield 136%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (1 ml) was added under cooling in an ice bath to the compound (10 mg) obtained in Example 70. The mixture was stirred for 2 hr. A saturated aqueous sodium hydrogencarbonate solution was then added to the reaction solution. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation. N,N-dimethylformamide (2 ml) was added to the residue to prepare a solution. Potassium carbonate (10 mg) and 3,3-diphenylpropyl bromide (4 mg) were then added to the solution. The mixture was stirred at room temperature overnight. Water was added to the reaction solution. The mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation. The residue was purified by preparative TLC (hexane:ethyl acetate=1:1) to give the title compound (10 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was then removed by distillation
  4. additionN,N-dimethylformamide (2 ml) was added to the residue
  5. customto prepare a solution
  6. stirringThe mixture was stirred at room temperature overnight
  7. extractionThe mixture was then extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was then removed by distillation
  10. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e606c21a3f2d4b6fb4fc472583095875
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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