Trifluoroacetic acid → HCID 21478946, compound

HRID 2292631Notes

Reaction equation

HRID 2292631 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([O:29]CC1C=CC=CC=1)=[CH:5][C:6]([C:13](=[O:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[N:7]2.FC(F)(F)C(O)=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:29])[CH:5]=[C:6]([C:13](=[O:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[NH:7]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90495Di-tert-butyl dicarbonateHCID 21478944HCID 21478944, compound

Product 1

HCID 21478946HCID 21478946, compound

Procedure

Combine 5,7-dichloro-2-[2-(t-butoxycarbonylamino) benzoyl]-4-benzyloxyquinoline (4 mmol) and trifluoroacetic acid (55 mL) and heat to 80° C. After 4 hours evaporate the reaction mixture in vacuo to give a residue. Add dichloromethane and evaporate several times to completely remove residual trifluoroacetic acid. Dissolve the crude reaction mixture in dichloromethane (20 mL) and add di-t-butyl dicarbonate (4 mmol). Allow to stir for 24 hours. Evaporate in vacuo. Chromatograph on silica gel to give the title compound.

Workup

  1. customAfter 4 hours evaporate the reaction mixture in vacuo
  2. customto give a residue
  3. customAdd dichloromethane and evaporate several times to completely remove residual trifluoroacetic acid
  4. dissolutionDissolve the crude
  5. customreaction mixture in dichloromethane (20 mL)
  6. customEvaporate in vacuo

Sources & evidence

ORD record
ord-34715578267d48d3b76c4cd86a726bee
Source dataset
uspto-grants-1997_11
Patent number
US05684017

Reaction notes

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