[CH2:1]([O:3][C:4]([C:6]1[C:10]2[C:11](=O)[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].[C:22]([NH:25][NH2:26])([NH2:24])=[NH:23].[ClH:27].Cl>C(O)C>[ClH:27].[CH2:1]([O:3][C:4]([C:6]1[C:10]2/[C:11](=[N:26]/[NH:25][C:22]([NH2:24])=[NH:23])/[CH2:12][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]To a mixture of 3-ethoxycarbonyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.28 g) and aminoguanidine hydrochloride (111 mg) were ethanol (20 ml) and 6N hydrochloric acid (0.086 ml), and the mixture was stirred at 90° C. for 2 hours and cooled. The reaction solution was concentrated under reduced pressure, and the residue was washed with ethanol, ethyl acetate and isopropylether, and dried to give (E)-3-ethoxycarbonyl-4-guanidinoimino-6-phenyl-4,5,6,7-tetrahydrobenzofuran hydrochloride (Compound 55) (0.25 g).
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