Trifluoroacetic acid → HCID 57205555, compound

HRID 2396372Notes

Reaction equation

HRID 2396372 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](=[O:33])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=3[Cl:19])[N:12](C(OC(C)(C)C)=O)[C:11]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:33])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=3[Cl:19])[NH:12][C:11]=2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21460731HCID 21460731, compound

Product 1

HCID 57205555HCID 57205555, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(p-chlorophenacyl)methylamino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (15 mL). Add trifluoracetic acid (5 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 (1.3 g).

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-64856d84395148a5b800684211dba1c5
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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