Diisopropylethylamine → HCID 86701006, compound

Participants

Reaction Steps

DIPEA (3.7 g, 10 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (1.45 g, 5.3 mmol) and tert-butyl 4-(hydrazinecarbonyl)piperazine-1-carboxylate, (1.6 g, 6.6 mmol) in dry DMF (50 mL) at 0° C., followed by the addition of HATU (1.45 g, 5.3 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water (200 mL), and the resulting precipitation was collected by filtration, rinsed with water, and then recrystallized (3:1 petroleum ether/EtOAc) to afford tert-butyl 4-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)piperazine-1-carboxylate (1.4 g, 54%), ESI-MS (EI+, m/z): 503 [M+H]+.

Provenance & Evidence