t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxy-2,5-dimethylphenoxy)phenyl}-N-methylcarbamate → 5-{4-[6-(4-Hydroxy-2,5-dimethylphenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

HRID 2303800Notes

Reaction equation

HRID 2303800 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:44]=[CH:43][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]=[C:29]([CH3:31])[C:28]([OH:32])=[CH:27][C:26]=4[CH3:33])=[CH:20][C:19]=3[N:34]([CH3:42])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:45].O1CCOCC1.Cl.C(OCC)(=O)C>C(#N)C.O>[ClH:45].[OH:32][C:28]1[C:29]([CH3:31])=[CH:30][C:25]([O:24][C:21]2[CH:22]=[CH:23][C:18]3[N:17]=[C:15]([CH2:14][O:13][C:12]4[CH:43]=[CH:44][C:9]([CH2:8][CH:4]5[S:3][C:2](=[O:1])[NH:6][C:5]5=[O:7])=[CH:10][CH:11]=4)[N:34]([CH3:42])[C:19]=3[CH:20]=2)=[C:26]([CH3:33])[CH:27]=1

Participants

5

Reactant 3

HCID 18461362t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxy-2,5-dimethylphenoxy)phenyl}-N-methylcarbamateHCID 204431481,4-Dioxane hydrochlorideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 867584455-{4-[6-(4-Hydroxy-2,5-dimethylphenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of t-butyl N-{2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxyacetylamino]-5-(4-hydroxy-2,5-dimethylphenoxy)phenyl}-N-methylcarbamate (0.71 g) and 4N hydrogen chloride/dioxane (10 ml) was stirred at room temperature for 17 hours. The solvent of the reaction mixture was evaporated to dryness. To the residue was added ethyl acetate and insoluble product was isolated by filtration and subjected to reversed-phase high performance liquid chromatography using acetonitrile/water=9/11 as the eluant and then treated with 4N hydrogen chloride/ethyl acetate to give the title compound (0.41 g).

Workup

  1. customThe solvent of the reaction mixture was evaporated to dryness
  2. additionTo the residue was added ethyl acetate
  3. custominsoluble product was isolated by filtration

Sources & evidence

ORD record
ord-351acfaf124f48b6a879a7fc8fa0d83f
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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