O.NN.CSCON1C(=O)C2=CC=CC=C2C1=O.Cl.[CH3:20][S:21][CH2:22][O:23][NH2:24].[CH:25]([NH:27][C:28]1[S:29][C:30]([Cl:40])=[C:31]([C:33](=O)[C:34]([O:36]CC)=[O:35])[N:32]=1)=[O:26].[OH-].[K+]>CO.O1CCCC1.N1C=CC=CC=1>[CH3:20][S:21][CH2:22][O:23][N:24]=[C:33]([C:31]1[N:32]=[C:28]([NH:27][CH:25]=[O:26])[S:29][C:30]=1[Cl:40])[C:34]([OH:36])=[O:35]
A solution of hydrazine hydrate (2.3 g) in methanol (2.3 g) was added to a mixture of N-(methylthiomethoxy) phthalimide (10.2 g) in tetrahydrofuran (30 ml) and stirred at ambient temperature for 30 minutes. 10% Hydrochloric acid (18 ml) was added to the reaction mixture under ice-cooling and the insoluble materials were filtered off to give a solution containing methylthiomethoxyamine. On the other hand, ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate (10 g) was added to the 1 N aqueous potassium hydroxide (76.2 ml) at ambient temperature and the mixture was stirred for 10 minutes. The reaction mixture was adjusted to pH 2.0 with 10% hydrochloric acid under ice-cooling, thereto were added pyridine (10 g) and the above solution containing methylthiomethoxyamine, followed by stirring at ambient temperature for 3 hours. The aqueous solution was adjusted to pH 7.5 with 10% aqueous potassium hydroxide and washed with ethyl acetate. Ethyl acetate was added to the aqueous solution and the resulting mixture was adjusted to pH 1.7 with 10% hydrochloric acid, and the separated organic layer was washed with 3% hydrochloric acid and water, dried over magnesium sulfate and evaporated to give 2-methylthiomethoxyimino-2-(2-formamido-5-chlorothiazol-4-yl)acetic acid (syn isomer)(8.1 g).
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