Trifluoroacetic acid → HCID 57218636, compound

HRID 2082531Notes

Reaction equation

HRID 2082531 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:36]=[CH:35][C:6]([C:7](=[O:34])[CH2:8][CH2:9][NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[N:13](C(OC(C)(C)C)=O)[C:12]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:36]=[CH:35][C:6]([C:7](=[O:34])[CH2:8][CH2:9][NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[NH:13][C:12]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21460681HCID 21460681, compound

Product 1

HCID 57218636HCID 57218636, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(p-trifluoromethylphenacyl)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 (820 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-14a2da3786644e43b0c4ca9c0b557401
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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