Sodium hydride → 4-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate

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Reaction Steps

To a solution of 360 mg of di-tert-butyl (5S)-2-(benzyloxycarbonyl)-5-[(tert-butoxy-carbonyl)amino]hexanedioate (0.71 mmol; see example 12f) in N,N-dimethyl formamide (10 mL) was added under argon atmosphere 26 mg of sodium hydride (60% in oil, 0.64 mmol). The resulting mixture was stirred at room temperature for 30 minutes. A solution of 197 mg 5-(benzyloxy)-2-(bromomethyl)pyridine (prepared according to example 17a; 0.71 mmol) in N,N-dimethylformamide (5 mL) was added, and the mixture was stirred at 60° C. for one hour. After cooling to room temperature, the mixture was concentrated in vacuo and the residue was purified by preparative HPLC (method A) to give 327 mg of the title compound (65% yield).

Provenance & Evidence