Trifluoroacetic acid → HCID 57265194, compound

HRID 1488831Notes

Reaction equation

HRID 1488831 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-6b7fc0aa758c4b179da5f75ec9e07c91
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

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