[F:1][C:2]1([F:25])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:14][C:9]=2[S:8][C:7]1=[O:24].[OH:26]O>O1CCOCC1.O.CO.CN1C(=O)CCC1>[F:1][C:2]1([F:25])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:26])=[CH:14][C:9]=2[S:8][C:7]1=[O:24]To a solution of 3-[(2,2-difluorocyclopropyl)methyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2(3H)-one (18-1) (0.483 g, 1.32 mmol) in anhydrous 1,4-dioxane (5 mL) was added a 30% by weight solution of hydrogen peroxide in water (0.537 mL, 5.26 mmol. The reaction mixture was then stirred at room temperature for 0.5 hours. The crude reaction mixture was diluted with methanol and NMP, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 5% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) gave 3-[2,2-difluorocyclopropyl)methyl]-6-hydroxy-1,3-benzothiazol-2(3H)-one (18-2) as a tan solid. HRMS (M+H)+: observed=258.0396, calculated=258.0395.
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