Trifluoroacetic acid → HCID 67619096, compound

HRID 1941405Notes

Reaction equation

HRID 1941405 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[C:5](=[O:30])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[N:11](C(OC(C)(C)C)=O)[C:10]=1[C:26]([O:28][CH3:29])=[O:27].FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[C:5](=[O:30])[CH2:6][CH2:7][NH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22906431HCID 22906431, compound

Product 1

HCID 67619096HCID 67619096, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-[(3,4-difluorophenacyl)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-778e80b761b14a30ad33fdd85fdd9406
Source dataset
uspto-grants-1997_12
Patent number
US05703107

Reaction notes

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