C(O[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+].Cl.[NH:18]([O:20][CH3:21])[CH3:19].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CCO.CN(C=O)C>[CH2:12]([O:11][C:9]1[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=1)[C:4]([N:18]([O:20][CH3:21])[CH3:19])=[O:14])[CH3:13]To a solution of 16-2 (15 g, 72 mmol) in EtOH (100 mL) was added 1N NaOH (80 ml, 80 mmol). After stirring for 1 h, the solvents were evaporated and the residue was dissolved in 1N HCl (80 ml, 80 mmol) and then concentrated, azeotroped with CH3CN to give the crude acid. The crude acid was suspended in DMF (200 mL) and then treated with HCl.HN(Me)OMe (13.9 g, 144 mmol), EDC (15.1 g, 79.2 mmol), HOBT (9.6 g, 72 mmol) and NMM (60 mL, 576 mmol). The mixture was stirred for 18 hours and then concentrated. The residue was dissolved in ethyl acetate, washed with 10% K2CO3, brine, dried (MgSO4), and concentrated to give amide 16-3 as a brown oil.
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