Trifluoroacetic acid → HCID 67619204, compound

HRID 1488805Notes

Reaction equation

HRID 1488805 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 trifluoracetic acid (5 mL) and stir for 4 hours at room temperture. 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-fa799dda624b4ad6b3784bc069e8e895
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

Loading…