Hydrochloric Acid → (E)-4-(2-(4-((2,4-Dioxothiazolidin-5-ylidene)methyl)phenoxy)ethoxy)benzoic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl ester 356 (647 mg, 1.62 mmol) in THF (15 mL) was added methanol (2 mL), water (2 mL) and lithium hydroxide monohydrate (340 mg, 8.11 mmol). The mixture was heated at 60° C. for 1 hour, acidified with 10% HCl solution and extracted with ethyl acetate. The organic extract was dried over MgSO4, filtered, and evaporated to afford the title compound (141 mg, 22%). 1H NMR: (MeOD-d4) δ (ppm): 7.97 (d, J=8.8 Hz, 2H), 7.75 (s, 1H), 7.53 (d, J=8.8 Hz, 2H), 7.12 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 4.44 (4H, bs). LRMS (ESI): (calc.) 385.4; (found) 392.3 (MLi)+.

Provenance & Evidence