Methyl iodide → Ammonium Acetate

Participants

Reaction Steps

To a solution of Example 128 (32.0 mg, 0.09 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (Aldrich, 3.7 mg, 0.15 mmol) and methyl iodide (Aldrich, 15.6 mg, 0.11 mmol). The reaction mixture was stirred at room temperature overnight then quenched with saturated aqueous NaHCO3 and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative high pressure liquid chromatography on a waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.47-1.64 (m, 4H), 1.62-1.84 (m, 4H), 2.03-2.18 (m, 2H), 2.27 (s, 2H), 2.27 (s, 3H), 2.50-2.62 (m, 1H), 3.24 (d, J=1.4 Hz, 3H), 3.24 (s, 3H), 3.64 (t, J=5.8 Hz, 2H), 4.26 (t, J=5.8 Hz, 2H), 4.45 (s, 2H); MS (ESI+) m/z 365 (M+H)+; Anal. Calculated for C19H28N2O3S: C, 62.61; H, 7.74; N, 7.69. Found: C, 62.62; H, 7.73; N, 7.85.

Provenance & Evidence