Lithium hydroxide, monohydrate → 4-(3-(Benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylic acid

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Reaction Steps

To a solution of ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylate (0.299 g, 0.540 mmol) in tetrahydrofuran (15 mL) and methanol (5 mL) at room temperature was added a solution of lithium hydroxide hydrate (0.091 g, 2.160 mmol) in water (2 mL). The resulting mixture was stirred at room temperature for 1.5 hr, and then concentrated under vacuum to almost dryness. To the residue was added water (8 mL), and the mixture was neutralized with 1N HCl to pH 4-5. The insoluble product (0.237 g, 0.451 mmol, 83% yield) was collected as a beige solid by suction filtration and dried over Drierite under vacuum.

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