Sodium Hydroxide → 2-(2-Methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acid

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Reaction Steps

To (2-methyl-imidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acid ethyl ester (4.0 g, 17.76 mmol) in 30 mL EtOH was added aqueous NaOH (1M, 19.5 mL) and the mixture was stirred at room temperature for 1 hour or until LC-MS showed complete consumption of starting material. To the mixture was added Amberlyst 15 (wet) ion-exchange resin (Aldrich) until the pH reached 5. The resin was removed by filtration and the filtrate was concentrated to obtain 1.7 g (50%) of the title compound (SM-1ae). Further purification was performed by trituration with water and ethyl ester to obtain a white solid. MS (ES+) 198.1 (M+H)+ 1H NMR (DMSO-d6) δ 2.66 (s, 3H), 3.53 (s, 2H), 7.86 (s, 1H), 12.31 (br s, 1H).

Provenance & Evidence