[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][NH:20][CH3:21])[C:12]3[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=3[S:10]2)=[CH:5][CH:4]=1.C(Cl)Cl.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[CH2:34][CH2:35]Cl.[I-].[Na+]>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:21])[CH2:35][CH2:34][C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([O:30][CH3:29])[CH:32]=3)[C:12]3[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=3[S:10]2)=[CH:7][CH:8]=1A mixture of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (1.07 g), methylene chloride (20 ml), 3-methoxyphenethyl chloride (500 mg), triethylamine (313 mg) and sodium iodide (30 mg) is stirred at room temperature for 48 hours. After the completion of the reaction, the solvent is distilled off, and the resulting residue is purified by silica gel column chromatography (eluent; chloroform: ethanol=15:1) to give (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-{2-[N-methyl-N-(3-methoxyphenethyl)amino]ethyl}-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (625 mg) as oily product.
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