Pyridine → HCID 117642556, compound

Participants

Reaction Steps

(COCl)2 (560 μL, 6.39 mmol) was added dropwise to a stirred solution of 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid (7) (1.6 g, 3.20 mmol) in DCM (20 mL) at 0° C., followed by 2 drops of DMF. The reaction mixture was stirred at RT for 5 h, concentrated in vacuo and the resulting residue was dissolved in DCM (15 mL). N,O-dimethylhydroxylamine was added (215 mg, 3.52 mmol) followed by pyridine (620 μL, 7.67 mmol), and the reaction allowed to stir at RT for 18 h. The mixture was diluted with DCM (25 mL) and water (50 mL), the organic layer was separated and washed with water (2×25 mL), brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The product was purified by silica gel chromatography (40 g, 0-80% EtOAc in isohexane) to afford 3,4-bis(benzyloxy)-N2-methoxy-1-(4-methoxyphenyl)-N2,N5,N5-trimethyl-1H-pyrrole-2,5-dicarboxamide (33) (505 mg, 22%) as a colourless oil. m/z 544 (M+H)+ (ES+).

Provenance & Evidence