Trifluoroacetic acid → HCID 57134806, compound

HRID 2082525Notes

Reaction equation

HRID 2082525 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4](=[O:31])[CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[N:10](C(OC(C)(C)C)=O)[C:9]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4](=[O:31])[CH2:5][CH2:6][NH:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:18])=[CH:14][C:15]=2[Cl:17])[NH:10][C:9]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21460751HCID 21460751, compound

Product 1

HCID 57134806HCID 57134806, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(o-fluorophenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (5 mL). Add trifluoracetic acid (3 mL) and stir for 5 hours. Concentrate the reaction in vacuo, dilute with ethyl acetate (100 mL), wash with saturated sodium carbonate, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound (650 mg).

Workup

  1. concentrationConcentrate
  2. customthe reaction in vacuo
  3. washwash with saturated sodium carbonate
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customRecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3f72b00c800c4e0f80d2b5cc616171ed
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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