Lithium Hydroxide → 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic Acid

Beteiligte Stoffe

Reaktionsschritte

To a solution of compound 118E (128 mg, 0.33 mmol) in THF (15 mL) was added 0.1 M aqueous LiOH (3.75 mL) and the mixture was stirred at room temperature. After 24 h, the resultant solution was acidified to pH 4 and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water (20 mL) and concentrated to give the crude product, which was further purified by chromatography on 70-230 mesh silica gel eluted with CH2Cl2:methanol:water 40:10:1 to afford 104 mg (0.29 mmol, 88%) of the product as a solid, mp 206-207° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.05 (s, 3H), 3.81 (s, 2H), 7.65 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 24.8, 37.3, 119.0, 127.5, 137.9, 142.6, 153.3, 169.4, 169.5, 170.9; MS (LCQ, ESI+) Calcd for C12H13N4O5S2 357.0. found 357.0 (M+H)+. HRMS (ESI+, m/z) Calcd for C12H13N4O5S2 357.0327. found 357.0326 (M+H)+.

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