C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=1.[I-].C[N+]1C=CC=CC=1Cl.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:41][CH:42]([CH2:46][CH3:47])[C:43](O)=[O:44])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:41][CH:42]([CH2:46][CH3:47])[C:43]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)=[O:44])(=[O:39])=[O:40])=[CH:36][CH:37]=1Triethylamine (1.99 ml), ethyl 4-aminophenylacetate hydrochloride (699 mg), and 1-methyl-2-chloropyridinium iodide (1.1 g) were added to a solution of (RS)-2-(4-chlorobenzenesulfonylamino)butanoic acid (1 g) in chloroform (30 ml), and the whole was heated under reflux for 2 hours under argon. The reaction mixture was concentrated under reduced pressure. After adding 1N HCl, the residue was extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 70 g, hexane/ethyl acetate=2/1) to give (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl) phenyl)butanamide (237 mg).
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