C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[N:6]=1)=[O:4].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[S:12]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)(=[O:14])=[O:13]5-Methyl-6-(piperidine-1-sulfonyl)-pyridine-2-carboxylic acid methyl ester (53 mg, 0.178 mmol) in dioxane (2 mL) was added to a solution of lithium hydroxide monohydrate (CAN 1310-66-3, 0.1 g, 2.38 mmol) in water (2 mL) and the mixture was stirred for 2 h at room temperature. The solvent was removed in vacuo, water (10 mL) was added, and the pH was adjusted to 3 with 1 N hydrochloric acid. The mixture was extracted by ethyl acetate (2×10 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, and concentrated to give the product (36 mg, 71%); MS (EI): m/e=285.2 [M+H]+.
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