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 2303800노트

반응식

HRID 2303800 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-351acfaf124f48b6a879a7fc8fa0d83f
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06432993B1

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