C([O:4][CH2:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[N:13]=1)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CO>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[N:13]=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[S:10][CH:11]=2)=[CH:19][CH:18]=12-{[4-(4-Bromophenyl)-1,3-thiazol-2-yl]amino}-2-oxoethyl acetate (1.1 g, 3.1 mmol), prepared in the previous step, was suspended in 20 mL of methanol and K2CO3 (0.43 g, 3.1 mmol) was added. The mixture was stirred for 2 h, then diluted using methylene chloride. The mixture was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (2% methanol/chloroform) provided N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamide (670 mg, 68%) as a white solid. mp 222-224° C. HRMS: calcd for C11H9BrN2O2S+H+, 312.96408; found (ESI, [M+H]+), 312.9651. Analytical HPLC: retention time 9.0 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.
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