Acetic Anhydride → HCID 89616791, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (120 mg, 0.35 mmol) in acetic anhydride (1 mL, 10.6 mmol) was added NaOAc (90 mg, 1.06 mmol), the suspension was stirred at 100° C. for 2 h. The reaction mixture was partitioned between DCM (25 mL) and iced water (25 mL), dried (MgSO4), filtered and volatiles removed in vacuo to afford a colourless oil. Trituration of the colourless oil from Et2O gave 2-(dimethylcarbamoyl)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl diacetate (UL1-044) (80 mg, 52%) as a white solid: m/z 433 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.27-7.11 (2H, m), 7.00-6.88 (2H, m), 4.00 (q, J=7.1 Hz, 2H), 3.79 (s, 3H), 2.79 (s, 3H), 2.71 (s, 3H), 2.26 (s, 6H) 1.05 (t, J=7.1 Hz, 3H).

Provenance & Evidence