Trifluoroacetic acid → HCID 9828084, compound

HRID 1637407Notes

Reaction equation

HRID 1637407 reaction equation
C([O:5][C:6](=[O:41])[C@@H:7]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[N:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:19]=2)=[CH:14][CH:13]=1)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:26]1[CH2:27][CH2:28][CH2:29][NH:30][C:25]=1[NH:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:10]([NH:9][CH2:8][C@H:7]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:6]([OH:41])=[O:5])=[O:11])=[CH:17][CH:16]=2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15887742HCID 15887742, compound

Product 1

HCID 9828084HCID 9828084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-9 (175 mg, 0.305 mmol), TFA (3 mL) and CH2Cl2 (3 mL) was stirred at ambient temperature for 3.0 hours. The reaction was concentrated and then azeotroped with toluene (3×10 mL). The residue was dissolved in 5:1 AcOH/HCl (36 mL). 10% Pd/C (150 mg) was added and the mixture was shaken under 62 psi of hydrogen gas for 2.0 hours. Following filtration and evaporative removal of the solvent, the residue was chromatographed (silica gel, 10:1:1 EtOH/ NH4OH/H2O) to give 1-10 as a colorless oil.

Workup

  1. concentrationThe reaction was concentrated
  2. customazeotroped with toluene (3×10 mL)
  3. dissolutionThe residue was dissolved in 5:1 AcOH/HCl (36 mL)
  4. addition10% Pd/C (150 mg) was added
  5. filtrationfiltration
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 10:1:1 EtOH/ NH4OH/H2O)

Sources & evidence

ORD record
ord-d73b967f4215470d92919269783fcdd9
Source dataset
uspto-grants-2000_03
Patent number
US06040311

Reaction notes

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