[NH2:1][C:2]([CH2:11][OH:12])=[CH:3][C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:13][C:14]1[C:15]([NH:20]N)=[N:16][CH:17]=[CH:18][CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[Cl:13][C:14]1[C:15]([N:20]2[C:4]([OH:10])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][C:2]([CH2:11][OH:12])=[N:1]2)=[N:16][CH:17]=[CH:18][CH:19]=1A mixture of ethyl 4-amino-5-hydroxy-2-oxopent-3-enoate (2.5 g, 14 mmol), 3-chloropyridin-2-ylhydrazine (2.07 g, 14 mmol) and p-toluenesulphonic acid monohydrate (2.5 g, 13 mmol) was stirred in 25 ml of acetonitrile at 25° C. for 5 hours. The precipitate was isolated by filtration and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography on SiO2 (eluent: hexane/ethyl acetate). Oil. Yield 4.2 g (90%).
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