[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.O.ClC(OCC(C)C)=O.Cl.NC1C=C(C(O)=O)C(O)=CC=1>CN(C=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]After 381.1 g (1.16 mole) of BOC-Arg-OH.HCl.H2O was dissolved in 1392 ml of DMF, 151 ml of NEM was added to the solution. Then, 152.3 ml of isobutyl chloroformate was dropwise added to the solution at -20° C. The resulting mixture was reacted for 10 minutes. After the reaction, 928 ml of a solution of 219.8 g (1.16 mole) of 5-aminosalicylic acid hydrochloride and 301.6 ml of NEM in DMF was dropwise added to the reaction solution at -15° to -10° C. After the dropwise addition, the mixture was reacted at the same temperature for 3 hours and further at room temperature for 15 hours. After the reaction, DMF was removed by distillation under reduced pressure and the residue was dissolved in 464 ml of MeOH and 332 ml of n-BuOH. To the solution was added 3300 ml of AcOEt. After washing twice with 2160 ml of cold 5% hydrochloric acid saturated with sodium chloride, the mixture was dried over anhydrous magnesium sulfate. After drying, magnesium sulfate was filtered off and the solvent was removed by distillation under reduced pressure to give 464.8 g (89.9%) of Boc-Arg-CHA.HCl.
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