HOAt → HCID 66811536, compound

Participants

Reaction Steps

To a solution of benzyl 3-(hydrazinocarbonyl)azetidine-1-carboxylate (350 mg, 1.40 mmol) in DMF (10 ml) were added 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (1A.5, 427 mg, 1.40 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (322 mg, 1.68 mmol), and 1-hydroxy-7-azabenzotriazole (95.3 mg, 0.700 mmol). The reaction was allowed to stir for 48 h, and then poured onto 10% potassium hydrogen sulfate and diluted with water (10 ml) and EtOAc (30 ml). The organic portion was isolated, washed with 3M lithium chloride (2×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 0-50% EtOAc/hexanes) to yield tert-butyl 2-{[2-({1-[(benzyloxy)carbonyl]azetidin-3-yl}carbonyl)hydrazino]carbonyl}-3-phenylpiperidine-1-carboxylate (31%).

Provenance & Evidence