Water → 2-(3,3-Dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid

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Reaction Steps

Water (2 mL) and methanol (8 mL) were added to ethyl 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate (185 mg, 0.57 mmol) and NaOH (27 mg, 0.675 mmol), and the resultant mixture was stirred at room temperature under a blanket of nitrogen as inert gas. To complete the reaction, NaOH (200 mg, 5 mmol) was again added, and stirring was continued for a further 24 hours at room temperature. Following removal of MeOH, 2M HCl (10 mL) was added, and the resultant mixture was extracted with CH2Cl2 (3×20 mL). Following drying of the combined organic phases over Na2SO4 and filtration, there was obtained the product 2-(3,3-dimethylbutyrylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid in a yield of 144 mg (corresponding to 85% of theory).

Provenance & Evidence