Triethylamine → (2S,5R)-6-(Benzyloxy)-N-[2-(dimethylamino)pyridin-4-yl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (37.3 mg, 0.135 mmol) in dry dichloromethane (2.5 mL) was added triethylamine (0.047 mL, 0.338 mmol), 2-chloro-1-methylpyridinium iodide (38.3 mg, 0.15 mmol), and 2-dimethylamino-4-aminopyridine (21.7 mg, 0.158 mmol) sequentially at room temperature under nitrogen. The reaction was then heated to 50° C. for 1.5 hours. LC/MS showed reaction complete. The reaction mixture was concentrated and purified by HPLC on a 30×100 mm Waters Sunfire column to afford the title compound as an off-white solid after lyophilization.

Provenance & Evidence