t-Butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-trifluoromethylphenoxy)phenyl}-N-methylcarbamate → 5-{4-[1-Methyl-6-(4-trifluoromethylphenoxy)-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

HRID 2303812Notes

Reaction equation

HRID 2303812 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:45]=[CH:44][C:12]([O:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[CH:20][C:19]=3[N:35]([CH3:43])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1>FC(F)(F)C(O)=O>[CH3:43][N:35]1[C:19]2[CH:20]=[C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH:22]=[CH:23][C:18]=2[N:17]=[C:15]1[CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])=[CH:45][CH:44]=1

Participants

3

Reactant 1

HCID 18461426t-Butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-trifluoromethylphenoxy)phenyl}-N-methylcarbamate

Product 1

HCID 778447575-{4-[1-Methyl-6-(4-trifluoromethylphenoxy)-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dioneYield 77.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-trifluoromethylphenoxy)phenyl}-N-methylcarbamate (0.95 g) in trifluoroacetic acid (20 ml) was stirred at 60° C. for 3 hours and allowed to stand at ambient temperature overnight. The reaction mixture was concentrated and to the residue was added water and neutralized with aqueous sodium bicarbonate solution (5%). The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then evaporated. The residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=1/2 as the eluant to give the title compound (0.60 g).

Workup

  1. concentrationThe reaction mixture was concentrated and to the residue
  2. additionwas added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-55fded05966d435d8d02e8cbccd1af06
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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