[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[O:37]([NH2:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C>[CH3:38][O:37][NH:39][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12]To a solution of 7-(2-naphthoyl)heptanoic acid 50 g (500 mg, 1.76 mmol) in DMF (10 mL) were added HOBT (309 mg, 2.29 mmol) and EDC (504 mg, 2.64 mmol). The mixture was stirred at room temperature for 1 hour, after which methoxylamine-HCl (176 mg, 2.11 mmol) and triethylamine (300 μL, 2.11 mmol) were added and the solution was stirred at room temperature for 16 hours, then at 45° C. for 2 hours. The DMF was evaporated under high vacuum, deionized water was added, and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated sodium bicarbonate (10 mL), washed with brine (10 mL), and dried (MgSO4). The solvents were removed in vacuo and the title compound 64 (308 mg, 56%) was isolated by recrystallization from acetone. 1H NMR (400 MHz, 5:1 CDCl3:CD3OD): 8.37 (s, 1H), 7.89 (m, 2H), 7.78 (m, 2H), 7.48 (m, 2H), 3.59 (s, 3H), 3.01 (t, J=7.3 Hz, 2H), 1.96 (t, J=7.3 Hz, 2H), 1.67 (m, 2H), 1.54 (m, 2H), 1.31 (m, 4H).
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