Tetrahydrofuran → HCID 21088583, compound

Reaction equation

[N:1]1([C:10]2[O:11][C:12]([CH2:22][CH2:23][C:24]([N:26]3[CH2:30][CH2:29][S:28][CH2:27]3)=[O:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:31]1CCCC1.ClC1C=CC=C(C(OO)=O)C=1>O>[N:1]1([C:10]2[O:11][C:12]([CH2:22][CH2:23][C:24]([N:26]3[CH2:30][CH2:29][S:28](=[O:31])[CH2:27]3)=[O:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Procedure

To a mixture of 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propanoyl}thiazolidine (25 mg) and tetrahydrofuran (10 mL) was added m-chloroperbenzoic acid (14.4 mg) with stirring under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and then with saturated brine, dried (MgSO4) and concentrated. The residue was introduced into preparative HPLC and purified to give 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propanoyl}thiazolidine-1-oxide (7.3 mg, yield 28%).