Trifluoroacetic acid → HCID 57265194, compound

HRID 2396376Notes

Reaction equation

HRID 2396376 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. Extract 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. extractionExtract into methylene chloride
  4. dry with materialdry (MgSO4)
  5. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-778386e51e2547f9b0446694f2f5cae8
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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