[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[OH:12])=[O:5])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[O:12][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])=[O:5])[CH3:2]To a solution of 4-hydroxy-2-methyl-thiazole-5-carboxylic acid ethyl ester (5.0 g, 26.74 mmol) in chloroform (80 mL) were added p-toluenesulfonyl chloride (5.61 g, 29.41 mmol) and triethylamine (4.84 mL, 34.76 mmol) at 0° C. The reaction mixture was allowed to warm to RT over 4 h, then diluted with DCM and H2O. The organic layer was isolated, washed with H2O and brine, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a pale brown solid (8.1 g, 89%).
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