Sodium Hydroxide → (2S,3R)-2-amino-3-hydroxy-N-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}butyramide

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Reaction Steps

190 mg (0.47 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine were dissolved in 5 ml of THF, and 86 mg (0.56 mmol) of 1-hydroxybenzotriazole hydrate, 239 μl (1.40 mmol) of N-ethyldiisopropylamine, 108 mg (0.56 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 113 mg (0.56 mmol) of N-(tert-butoxycarbonyl)-L-threonine were added. The mixture was stirred at room temperature overnight, dissolved in EA and 1 N NaOH and shaken. The organic phase was washed with water, dried over sodium sulfate, filtered and evaporated. The protecting group was cleaved off as already described using HCl in dioxane. The product was purified by means of preparative HPLC and is in the form of the hydrochloride.

Provenance & Evidence