Example 1 (82 mg, 0.19 mmol), (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyamine (see Bailey et al., J. Med. Chem., 34, 1991, 51-65; 56 mg, 0.38 mmol), and HOBt (28 mg, 0.21 mmol) were stirred in CH2Cl2 (4 mL) with DMF (0.5 mL) at r.t. EDC (47 mg, 0.25 mmol) and then triethylamine (40 μL, 0.29 mmol) were added, and the reaction stirred for 16 h. The solution was washed with 0.1N HCl and brine, dried (MgSO4), and concentrated in vacuo. The residue was stirred in MeOH (2.0 mL) and water (200 μL) with p-toluensulfonic acid (16 mg, 0.08 mmol) for 4 h. Triethylamine (50 μL) was added, and the solution was concentrated in vacuo. Purification by prep-HPLC gave 48 mg (48%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.50 (s, 1H), 8.04 (s, 1H), 7.57 (d, 1H, J=8.8 Hz), 7.40 (d, 1H, J=8.8 Hz), 6.79 (t, 1H, J=8.8 Hz), 4.00 (t, 2H, J=7.6 Hz), 3.77-3.84 (m, 1H), 3.63-3.68 (m, 2H), 3.28-3.36 (m, 2H), 3.17 (t, 2H, J=7.6 Hz), 2.01-2.09 (m, 2H). MS (ES) [m+H] calc'd for C18H18F2IN3O5, 522. found 522.
