Benzoic Acid → (6R,7aS)-2-(3,5-dichlorophenyl)-1,3-dioxohexahydro-1H-pyrrolo[1,2-c]imidazol-6-yl benzoate

Participants

Reaction Steps

To a solution of (6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione (1.2 g) (4 mmol) (Preparation 6), dimethylaminopyridine (50 mg) (0.1 eq.) and benzoic acid (0.49 g) (1 eq.) in 10 mL of dry DCM at 0° C. was added DCC (0.9 g) (1 eq.) in a minimal volume of DCM. The reaction mixture was stirred to RT overnight. After filtering off the insoluble material, the reaction mixture is washed with a dilute NaHCO3 aqueous solution, with dilute HCl solution, with water, dried over MgSO4, and evaporated under reduced pressure to afford to afford the titled compound as a viscous oil (1.54 g). 1H NMR (CDCl3): 8.05 (2H,d), 7.65 (1H,m), 7.5 (1H,d), 7.43 (2H,d), 7.38 (1H,m), 5.81 (1H,t), 4.62 (1H,dd), 4.23 (1H,dd), 3.56 (1H,d), 2.68 (1H,dd), 2.05–2.20 (1H,m).

Provenance & Evidence