Tetrahydrofuran → HCID 9845971, compound

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:28])[CH2:11][C:12]2[CH:17]=[C:16]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])=[CH:5][CH:4]=1.O1CCCC1>[Pd].C(O)C>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:28])[CH2:11][C:12]2[CH:17]=[C:16]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])=[CH:5][CH:4]=1

Participants

Procedure

N-[4-(Trifluoromethyl)phenyl]-2-[5-((2,4-dioxothiazolidin-5-ylidene)methyl]-2-methoxyphenyl]acetamide (300 mg, 0.687 mmol), 10% palladium on carbon (300 mg) and a mixed solvent of tetrahydrofuran and ethanol (2:1 v/v, 40 mL) were mixed, and hydrogenation was performed at room temperature and at an initial pressure of 392 kPa. After completion of the reaction, catalyst was filtered and the filtrate was concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=2:1 v/v) to obtain 172 mg (57%) of the title compound as colorless powder.