[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][Si:15]([CH3:19])([CH3:18])[CH2:14][CH2:13]1.C([O-])(O)=O.[Na+].[C:25](Cl)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C1COCC1.[Pd]>[CH2:28]([O:27][C:25](=[O:26])[NH:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:12]2[CH2:17][CH2:16][Si:15]([CH3:19])([CH3:18])[CH2:14][CH2:13]2)=[C:4]([F:11])[CH:5]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1To a solution of 9a (1.32 g, 4.61 mmol) in THF, Pd/C is added for hydrogenation under a pressure of 35 psi in a par hydrogenator. The reaction mixture is filtered through celite. To the filtrate, saturated NaHCO3 (1.16 g, 13.84 mmol), CBzCl (1.17 g, 6.93 mmol) are added and stirred at 25° C. for 5 h. The solvent is removed, 10 mL water is then added and the aqueous layer is extracted with EtOAc. The crude mixture is then subjected to column chromatography on silica gel using hexane-DCM mixtures to afford the product 10a as a viscous liquid (1.25 g) in 69% yield.
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