Trifluoroacetic acid → HCID 67619096, compound

HRID 2396331Notes

Reaction equation

HRID 2396331 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, compound

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 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 yieldthe 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-a77547fdde024b40b2fa7fd033125b6d
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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