Trifluoroacetic acid → HCID 67619204, compound

HRID 2396328Notes

Reaction equation

HRID 2396328 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([C:6](=[O:31])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[N:12](C(OC(C)(C)C)=O)[C:11]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:31])[CH2:7][CH2:8][NH:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67618227HCID 67618227, compound

Product 1

HCID 67619204HCID 67619204, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(p-fluorophenacyl)methylamino]-2-carbmethoxy-6-chloro-1-(tert-butyloxycarbonyl)-indole from above in methylene chloride (5 mL). Add trifluoraceticacid (5 mL) and stir for 4 hours at room temperature. Dilute with ethyl acetate (50 mL) and rinse with 1N sodium hydroxide, saturated sodium chloride, dry over magnesium sulfate, filter and concentrate in vacuo. Purify the residue by flash chromatography (30% ethyl acetate/hexane) and recrystallize from ethyl acetate/hexane to yield the title compound (1.0 g, 62%).

Workup

  1. washrinse with 1N sodium hydroxide, saturated sodium chloride
  2. dry with materialdry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography (30% ethyl acetate/hexane)
  6. customrecrystallize from ethyl acetate/hexane

Sources & evidence

ORD record
ord-be100d75c3a0407f85a96d02e7d7801f
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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