[C:1]([O:5][C:6](=[O:29])[C:7]([O:10]/[N:11]=[C:12](/[C:16]1[N:17]=[C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:19][CH:20]=1)\[C:13]([OH:15])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:37])C(=O)C1>CN(C)C=O>[C:1]([O:5][C:6](=[O:29])[C:7]([O:10]/[N:11]=[C:12](/[C:16]1[N:17]=[C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:19][C:20]=1[Cl:37])\[C:13]([OH:15])=[O:14])([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]A solution of (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (70 g, 147 mmol) and NCS (23.50 g, 176 mmol) in N,N-Dimethylformamide (DMF) (735 mL) was stirred at 40° C. for 2.5 h. The reaction was quenched by addition of H2O (2 L), EtOAc (1 L) and 5% aq. sodium thiosulfate soln (400 mL). The organic layer was separated, and washed with H2O (2×), brine, dried and evaporated to afford (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)acetic acid (69 g, 91% purity, 135 mmol, 92% yield) as a light yellow foaming solid. LCMS: (M+H)+: 464.2
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