C([O-])(O)=O.[Na+].[CH:6]1([C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21]([NH:23][C:24]2[S:25][C:26]([CH:29]=O)=[CH:27][N:28]=2)=[O:22])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.[NH2:32][OH:33]>C1COCC1>[CH:6]1([C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21]([NH:23][C:24]2[S:25][C:26]([CH:29]=[N:32][OH:33])=[CH:27][N:28]=2)=[O:22])=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10]1To a mixture of 2M aq NaHCO3 (5 mL) and 1-(2-cyclopentanecarbonyl-4-methyl-phenyl)-3-(5-formyl-thiazol-2-yl)-urea (72 mg, 0.2 mmol) in THF (5 mL) was added hydroxylamine hydrochloride (200 mg) at room temperature with stirring. The resulting mixture was heated at 60° C. for 12 h. The reaction mixture was cooled and extracted with ethyl acetate. The organic layer was washed (brine), dried (Na2SO4) and concentrated to obtain 1-(2-cyclopentanecarbonyl-4-methyl-phenyl)-3-[5-(hydroxyimino-methyl)-thiazol-2-yl]-urea (56 mg, 76%) as a mixture of syn and antisomers.
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