Trifluoroacetic acid → HCID 58499327, compound

HRID 910271Notes

Reaction equation

HRID 910271 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:42])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[N:25]([CH2:26][CH3:27])[C:24]([C@H:28]([NH:30][S:31]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=3)(=[O:33])=[O:32])[CH3:29])=[N:23][N:22]=2)[CH:15]=1)(C)(C)C>C(Cl)(Cl)Cl>[Cl:41][C:36]1[CH:35]=[C:34]([S:31]([NH:30][C@@H:28]([C:24]2[N:25]([CH2:26][CH3:27])[C:21]([O:20][C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=3)[C:13]([OH:42])=[O:12])=[N:22][N:23]=2)[CH3:29])(=[O:33])=[O:32])[CH:39]=[CH:38][C:37]=1[Cl:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58499743HCID 58499743, compound

Product 1

HCID 58499327HCID 58499327, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (0.12 ml) was added to a solution of the compound (260 mg) of Example 18 in chloroform (12.0 ml), and the mixture was stirred at room temperature for five days. The mixture was evaporated to remove the solvent, and the resulting crude product was purified by column chromatography (neutral OH SiO2, ethyl acetate/hexane=50-99%, methanol/chloroform=0-20%) and then recrystallized (methanol/chloroform/hexane) to give the titled compound (Compound 113) (101 mg, colorless powder).

Workup

  1. customThe mixture was evaporated
  2. customto remove the solvent
  3. customthe resulting crude product was purified by column chromatography (neutral OH SiO2, ethyl acetate/hexane=50-99%, methanol/chloroform=0-20%)
  4. customrecrystallized (methanol/chloroform/hexane)

Sources & evidence

ORD record
ord-8115b8d6d43e48d6b62339e025355e89
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

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