[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:14][C@H:10]2[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.C1(C)C(C)=CC=CC=1.N[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].CS(O)(=O)=O>CO>[OH:14][C@H:10]1[C:11](=[O:12])[NH:13][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C@H:9]1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide (966 mg) and xylene (10 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a mixture of 2-aminothiophenol (689 mg) and ferrous sulfate heptahydrate (0.11 mg) in methanol (0.1 ml) is added immediately into the reaction system, and the mixture is reacted at the same temperature for 5 minutes. To the reaction mixture is added methanesulfonic acid (48 mg), and the mixture is refluxed for 13 hours. The mixture is cooled with ice for two hours, and the precipitated crystals are collected by filtration, washed with methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (1.07 g).
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