4-Methylmorpholine → 4-(benzyloxy)-3-tert-butyl-N-(2-oxo-2-((1R,2S,5R)-7-oxo-6-aza-bicyclo[3.2.1]octan-2-ylamino)ethyl)benzamide

Participants

Reaction Steps

To a solution of 2-(4-(benzyloxy)-3-tert-butylbenzamido)acetic acid (418 mg, 1.22 mmol) in anhyd DMF (8 mL) was added (1R,2S,5R)-tert-butyl 2-amino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (287 mg, 1.11 mmol), BOP reagent (738 mg, 1.67 mmol), and N-methylmorpholine (366 μL, 3.34 mmol). The mixture was stirred at room temperature for 12 h under nitrogen atmosphere and then diluted with EtOAc (250 mL). The organic layer was washed with water (100 mL), 0.1 N HCl (100 mL), satd NaHCO3 (100 mL), and brine (50 mL), dried (Na2SO4), and concentrated in vacuo. 4-(benzyloxy)-3-tert-butyl-N-(2-oxo-2-((1R,2S,5R)-7-oxo-6-aza-bicyclo[3.2.1]octan-2-ylamino)ethyl)benzamide (713 mg, quant.) was isolated as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.81-6.93 (m, 8H), 6.69 (s, 1H), 5.15 (s. 1H); 5.16 (s, 1H), 4.13-4.06 (m, 4H), 3.20-2.80 (m, 2H), 2.40-1.30 (m, 6H), 1.52 (s, 9H), 1.42 (s, 9H); MS found: (M+H)+=564.

Provenance & Evidence