Trifluoroacetic acid → HCID 57311472, compound

HRID 2396366Notes

Reaction equation

HRID 2396366 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[C:5](=[O:32])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=2[Cl:18])[N:11](C(OC(C)(C)C)=O)[C:10]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28].FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[C:5](=[O:32])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:19])=[CH:15][C:16]=2[Cl:18])[NH:11][C:10]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21460743HCID 21460743, compound

Product 1

HCID 57311472HCID 57311472, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(m-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 (760 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-f25d8c66a385440fb2868c80f28e1776
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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