1,2-Dichloroethane → HCID 86660286, compound

Participants

Reaction Steps

To a solution of methyl (2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-(N′-hydroxycarbamimidoyl)pyridin-2-yl)pyrrolidine-2-carboxylate (0.320 g; 0.75 mmol) and Intermediate A1 (0.210 g; 0.82 mmol) in MeCN (3 mL) was added EDC (0.157 g; 0.82 mmol). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with pyridine (2 mL) and heated at 150° C. in the microwave for 30 minutes. The solvent was removed in vacuo and the residue dissolved in DCM. The mixture was washed with water and the organic phase passed through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (6:1) to afford the title product. 1H NMR (CDCl3, 400 MHz) δ 8.69 (1H, d, J=2 Hz), 8.30 (1H, d, J=1.6 Hz), 8.15 (1H, d, J=1.6 Hz), 8.06-8.03 (1H, m), 7.24-7.16 (4H, m), 7.04 (1H, d, J=7.2 Hz), 4.82 (1H, m), 4.50 (1H, m), 4.22-4.18 (1H, m), 4.13-4.12 (2H, m), 3.76 (1H, m), 3.64 (3H, s), 3.23 (3H, s), 2.20 (1H, m), 1.99-1.98 (4H, m), 0.79 (9H, s), 0.00 (3H, s), −0.02 (3H, s).

Provenance & Evidence