Trifluoroacetic acid → HCID 57311472, compound

HRID 1488827Notes

Reaction equation

HRID 1488827 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-ecdf263614a84ce487d93b92a1ee8171
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

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