C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](=[O:28])(=[O:27])[N:11]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19].CCN(CC)CC.CCOCC.Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl.O>[CH3:26][O:25][C:23]([C:22]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:20])([F:21])[F:19])[S:10](=[O:28])(=[O:27])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]=1[OH:2])=[O:24]
In a 250 mL dry RB flask, 4.50 mL of TiCl4 (40.8 mmol) was dissolved in 100 mL of CH2Cl2 and was cooled to −30° C. A solution of 2-[methoxycarbonyl-methyl-(2-trifluoromethyl-phenyl)-sulfamoyl]-benzoic acid methyl ester (8.0 g, 18.54 mmol) in 50 mL CH2Cl2 was added dropwise. The resulting solution was kept at −30° C. for 30 minutes and was then cooled to −78° C. Et3N (7.75 mL, 55.6 mmol) in 50 mL CH2Cl2 was slowly syringed in resulting a dark red solution. The reaction mixture was stirred at −78° C. for 4 hours and was then poured into a 1-L flask containing 250 mL of Et2O, 100 mL concentrated HCl, and 100 mL of H2O. The mixture was stirred at room temperature overnight. The layers were separated, and the organic layer was washed with brine and dried over MgSO4. Upon evaporation of the solvent, light yellowish crystals of 4-hydroxy-1,1-dioxo-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester were formed. The product was collected through filtration and dried in oven to provide 2.2 g, 86% yield.
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