[ClH:1].[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1C=CC(Cl)=CC=1.Cl.CN(C)CCCN=C=NCC.[OH2:28].ON1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.CN1CCOCC1>C(Cl)Cl.C(O)=O>[CH3:2][O:3][C:4](=[O:15])[CH:5]([NH:6][CH:7]=[O:28])[CH2:14][C:33]1[CH:38]=[CH:37][C:36]([Cl:1])=[CH:35][CH:34]=1(±)-(4-Chlorophenyl)alanine methyl ester hydrochloride (2.00 g) was suspended in methylene chloride (20 mL), and to the suspension were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.60 g), 1-hydroxybenzotriazole monohydrate (1.23 g), N-methylmorpholine (1.90 mL), and formic acid (0.30 mL), followed by stirring for 15 minutes. Subsequently, formic acid (0.30 mL) addition and subsequent stirring for 15 minutes were repeated 3 times. The reaction mixture was diluted with methylene chloride. The organic layer was washed with water, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1), to thereby give the title compound (1.21 g).
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