Trifluoroacetic acid → HCID 57265194, compound

HRID 1941428Notes

Reaction equation

HRID 1941428 reaction equation
[C:1]1([S:7]([CH2:10][NH:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:29])=[C:18](C(OC(C)(C)C)=O)[C:19]=3[Cl:21])[NH:14][C:13]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([S:7]([CH2:10][NH:11][C:12]2[C:20]3[C:15](=[CH:16][C:17]([Cl:29])=[CH:18][C:19]=3[Cl:21])[NH:14][C:13]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67705862HCID 67705862, compound

Product 1

HCID 57265194HCID 57265194, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-[(phenylsulfonyl)methylamino]-2-carbethoxy-4,6-dichloro-tert-butyloxycarbonyl-indole (400 mg, 0.758 mmol) in methylene chloride (15 mL). Add, by dropwise addition, trifluoroacetic acid (15 mL) and stir at room temperature for 3 hours. Evaporate the solvent in vacuo and treat the resulting residue with saturated sodium hydrogen carbonate. Extact into methylene chloride and dry (MgSO4). Recrystallize (ethyl acetate/hexane) to give the title compound (70 mg, 22%); mp 244°-45° C.

Workup

  1. customEvaporate the solvent in vacuo
  2. additiontreat the resulting residue with saturated sodium hydrogen carbonate
  3. dry with materialExtact into methylene chloride and dry (MgSO4)
  4. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1b86c02b55324c8f90d40a2b93a71da5
Source dataset
uspto-grants-1997_12
Patent number
US05703107

Reaction notes

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