C(OC(C1[C:13]([C:14]([O:16]C)=O)=[CH:12][C:11]([Cl:18])=[N:10][CH:9]=1)=O)(C)(C)C.[C:19]([O:23][C:24]([C:26]1C(C(O)=O)=CC(Cl)=NC=1)=[O:25])(C)(C)C.[H-].[Na+].CI.[CH3:40][N:41]([CH:43]=[O:44])[CH3:42]>O>[Cl:18][C:11]1[CH:12]=[C:13]2[C:40](=[CH:9][N:10]=1)[N:41]([CH3:42])[C:43](=[O:44])[C:26]([C:24]([O:23][CH3:19])=[O:25])=[C:14]2[OH:16]Methyl 5-(tert-butoxycarbonyl)-2-chloroisonicotinate. To a solution of 5-(tert-butoxycarbonyl)-2-chloroisonicotinic acid (1 g, 3.7 mmol) in dry DMF (10 mL) was added NaH (60% suspension in mineral oil, 0.37 g, 9.24 mmol) in small portions with stirring and cooling using an ice-bath. After addition, the reaction mixture was treated with MeI (0.524 mL, 9.24 mmol) dropwise, and then stirred at room temperature for 1 hour. The reaction mixture was poured into water and stirred at room temperature for 3 hours. The precipitate was filtered and dried in vacuo to afford the title compound as a solid.
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