{(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic Acid Tert-butyl Ester → {3-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylpropyl}-carbamic Acid Tert-butyl Ester

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Reaction Steps

A solution of {(E)-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic acid tert-butyl ester (105 mg, 0.2 mmol) in ethanol (5 mL) is hydrogenated over 10% Pd/C at 1 atm for 18 h. The catalyst is removed by filtration through Celite and the solvent is removed under reduced pressure to give the title compound. It is converted to a potassium salt by addition of 1 equivalent of KHCO3. 1H NMR (400 MHz, MeOD) δ ppm 1.17 (s, 6 H) 1.34 (s, 9 H) 1.77-1.87 (m, 2 H) 2.35-2.44 (m, 2 H) 4.20 (s, 2 H) 6.59 (dd, J=8.08, 1.77 Hz, 1 H) 6.65 (d, J=1.77 Hz, 1 H) 7.20 (d, J=8.08 Hz, 1 H) LCMS (method A) retention time=1.32 min, (M−H)−=142

Provenance & Evidence