[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:19][OH:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1.[O-:27]S([O-])=O.[Na+].[Na+]>C(#N)C.O.CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)=[C:9]([C@H:18]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:19]([OH:27])=[O:20])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1To a solution of (S)-2-(2-amino-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethanol (1.95 g, 5.00 mmol) in acetonitrile (25 mL) and water (1 mL) was added H5IO6 (1.37 g, 6.00 mmol) and CrO3 (1.00 g, 10.0 mmol). The mixture was stirred at rt for 1 h and was diluted with EtOAc (50 mL) and a saturated solution of Na2SO3 (50 mL). The layers were separated, and the aqueous layer was extracted with EtOAc. The crude material was taken on without further purification. 1H-NMR: 400 MHz, (CDCl3) δ: 7.42-7.61 (m, 4H), 7.20 (s, 1H), 5.11 (s, 1H), 2.47 (s, 3H), 0.93 (s, 9H).
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