Trifluoroacetic acid → HCID 10562391, compound

HRID 479381Notes

Reaction equation

HRID 479381 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[N:18]1([C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)=[CH:25][CH:26]=2)[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11797643HCID 11797643, compound

Product 1

HCID 10562391HCID 10562391, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution in methylene chloride (1 ml) of 1,4-bis(4-tert-butoxycarbonyl-1-piperazinyl)benzene (59 mg; 0.13 mmol) synthesized by the above process under ice cooling, and the mixture was stirred for 30 minutes. The reaction mixture was then concentrated under reduced pressure, and the resultant concentrated residue (81 mg) was dissolved in methanol-chloroform (1:2). The solution was applied to a column packed with alumina (3 g), and the column was eluted with methanol-chloroform (1:2). The eluate was concentrated under reduced pressure, thereby obtaining 31 mg (yield: 88%) of the title compound as a colorless oil.

Workup

  1. customsynthesized by the above process under ice cooling
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. dissolutionthe resultant concentrated residue (81 mg) was dissolved in methanol-chloroform (1:2)
  4. washthe column was eluted with methanol-chloroform (1:2)
  5. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69daf64b3e8648d2959579a3aaa26ce6
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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