COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)[C:11]([OH:14])([CH3:13])[CH3:12])(=[O:9])=[O:8].FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>ClCCl>[Br:21][C:17]1[CH:16]=[C:15]([CH:10]([S:7]([NH2:6])(=[O:8])=[O:9])[C:11]([OH:14])([CH3:12])[CH3:13])[CH:20]=[CH:19][CH:18]=1A solution of 8.63 g of N-[2,4-dimethoxybenzyl]-1-(3-bromophenyl)-2-hydroxy-2-methylpropane-1-sulfonamide in 40 ml of dichloromethane was admixed with 10 ml of trifluoroacetic acid and stirred at room temperature for 30 minutes. The reaction solution was admixed with 40 ml of water, and gradually and cautiously with 150 ml of a saturated aqueous sodium hydrogencarbonate solution. The precipitate was filtered off with suction, washed with water and dried over P2O5 under reduced pressure. The crude product was purified by means of normal phase chromatography using a Flashmaster with a dichloromethane/methanol gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (4.11 g) with a molecular weight of 308.2 g/mol (C10H14BrNO3S); MS (ESI): m/e=325 (M+H2O+H+).
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