t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(3-phenylphenoxy)phenyl}-N-methylcarbamate → 5-{4-[1-Methyl-6-(3-phenylphenoxy)-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride
Reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:47]=[CH:46][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][CH:28]=[C:27]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:26]=4)=[CH:20][C:19]=3[N:37](C)[C:38](=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1.[ClH:48].O1CCOCC1>>[ClH:48].[CH3:38][N:37]1[C:19]2[CH:20]=[C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:26]=3)[CH:22]=[CH:23][C:18]=2[N:17]=[C:15]1[CH2:14][O:13][C:12]1[CH:46]=[CH:47][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1Participants
3
Reactant 2
Product 1
Procedure
A mixture of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(3-phenylphenoxy)phenyl}-N-methylcarbamate (2.57 g) and 4N hydrogen chloride/dioxane (30 ml) was stirred at room temperature for 63 hours. The solvent of the reaction mixture was evaporated to dryness and to the residue was added ethyl acetate and insoluble product was isolated by filtration and washed with ethyl acetate to give the title compound (2.01 g).
Workup
- customThe solvent of the reaction mixture was evaporated to dryness and to the residue
- additionwas added ethyl acetate
- custominsoluble product was isolated by filtration
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-7052303a61a5424e8be5ab419284944b
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06432993B1
Reaction notes
Loading…