COC1C=C(OC)C=CC=1C[N:6]([C:24]1[S:28][N:27]=[CH:26][N:25]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=[CH:13]2)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O.CO.[OH-].[Li+]>C(Cl)Cl.C1COCC1.O>[S:28]1[C:24]([NH:6][S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)(=[O:8])=[O:9])=[N:25][CH:26]=[N:27]1Methyl 6-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoate (7.10 g, 14.21 mmol) was dissolved in 100 mL of DCM and TFA (10.95 ml, 142 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The material was concentrated, dissolved in methanol, and re-concentrated to afford a light yellow solid. The solid was dissolved in THF (47.4 ml), methanol (47.4 ml), and water (47.4 ml). Lithium hydroxide (1.021 g, 42.6 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was concentrated and dissolved in concentrated HCl solution. The solution was stirred for 5 minutes and filtered. The resulting white solid was washed with water, dried under a nitrogen blanket, and collected to afford 6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-1-naphthoic acid (Intermediate MM) as an off-white solid. m/z (ESI) 336.2 (M+H)+.
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