3-{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-vinyl}-benzamide → 3-{2-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-benzamide

Participants

Reaction Steps

To a solution of 3-{2-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-vinyl}-benzamide in ethanol (2 mL) is added two equivalents of KHCO3. The mixture is diluted with 5 mL water and hydrogenated at 1 atm over 50 mg of 10% Pd/C for 18 h. The catalyst is filtered and the filtrate lyophilized. The resulting solid is purified by HPLC to give the title compound as an amorphous powder: m/z (M−1)−=374; 1H NMR (DMSO-d6) δ 7.95 (m, 1H), 7.81 (s, 1H), 7.72 (m, 1H), 7.35 (m, 4H), 6.75 (d, J=1.5 Hz 1H), 6.70 (m, 1H), 4.04 (s, 2H), 2.86 (m, 4H).

Provenance & Evidence