ClC([O:4][CH3:5])=O.CN1CC[O:10][CH2:9][CH2:8]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:21][C:22](=[O:29])[C:23](=[CH:27][CH:28]=2)[C:24]([OH:26])=[O:25])=[CH:16][CH:15]=1.[Si](Cl)(C)(C)[CH3:31].[CH3:35][C:36]#[N:37]>C(Cl)Cl.C(O)(C)C.CCN(CC)CC>[C:9]([N:13]([C:5](=[O:4])[C:36]([NH2:37])([CH3:31])[CH3:35])[C:14]1[CH:15]=[CH:16][C:17]([C:20]2[NH:21][C:22](=[O:29])[C:23](=[CH:27][CH:28]=2)[C:24]([OH:26])=[O:25])=[CH:18][CH:19]=1)(=[O:10])[CH3:8]
Methyl chloroformate, 1.7 ml (20 mM), was added to a solution of 2.9 g (20 mM) of alpha-acetamidoisobutyic acid, 2.2 ml (20 mM) of N-methylmorpholine in 50 ml CH3CN at -15° C. The mixture was stirred at -20° C. to -10° C. for 1/2 hr and to it was added in a dropwise manner preformed silylated pyridone solution (by stirring a mixture of 2.3 g (10 mM) of the 6-(4-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 3.84 ml (30 mM) of Me3SiCl, 4.2 ml (30 mM) of Et3N in 100 ml CH2Cl2 for 40 min) at -10° C. After the addition, the mixture was allowed to stir at 0° C. for 2 hrs and at room temperature for 12 hrs. To the resulting suspension was added 10 ml of isopropanol, stirred for 10 min, and the solids filtered, washed with MeOH, ether, dried to give 2.5 g of 6-[4-(N-acetyl-alpha-amino-isobutyrylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.
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