Iodine → HCID 86632123, compound

Participants

Reaction Steps

A solution of 2.00 g (3.99 mmol) N-Boc-2-(3-{2-[2-(2-{2-aminoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane 13 in 50 ml of acetone was treated with iodine (100 mg, 10% n/n) and stirred at room temperature for 60 minutes. Acetone was removed and replaced by ethyl acetate. The organic phase was washed with diluted sodium thiosulfate solution, water and brine and dried over magnesium sulfate. After removal of the solvent 1.17 g (3.74 mmol, 94%) of a slightly yellow oil remains. 1H-NMR (CDCl3) δ=9.85 (s, 1H), 7.16 (d, 1H, J=1.8 Hz), 7.13 (d, 1H, J=1.8 Hz), 5.00 (br, 1H), 4.25 (m, 2H), 3.95 (s, 3H), 3.92 (s, 3H), 3.89 (m, 2H), 3.74 (m, 2H), 3.70-3.59 (m, 6H), 3.53 (t, 2H, J=5.0 Hz), 3.30 (t, 2H, J=5.0 Hz), 1.44 (s, 9H) ppm. 13C-NMR δ=144.3, 131.6, 109.1, 106.6, 79.1, 70.8, 70.6, 70.5, 70.2, 70.1, 69.6, 69.0, 60.9, 56.2, 40.5, 28.3 ppm. MS: m/z=480 [M+Na]+, 358 [M-(COOtBuH2)]+. HRMS: Calcd. for C22H35NO9Na+480.2204, found 480.2203.

Provenance & Evidence