[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[C:13]([O:17][C:18]([O:20]C(OC(C)(C)C)=O)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]A suspension of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 100 mmol), di-t-butyldicarbonate (26.2 g, 120 mmol) and 4-dimethylaminopyridine (800 mg, 6.55 mmol) in dry tetrahydrofuran (300 mL) was stirred under nitrogen for 18 h. The solvent was evaporated in vacuo. The residue was suspended in dichloromethane (1 L) and filtered through a pad of celite. The filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine, dried (MgSO4), and concentrated in vacuo. The residue was triturated with hexanes. The solid was filtered and dried in vacuo to obtain the title compound (20 g, 72%) as a tan solid.
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