4-Methylmorpholine → HCID 89625018, compound

Participants

Reaction Steps

Isobutyl chloroformate (410 μL, 3.16 mmol) was added dropwise to a stirred solution of 3-methoxypropanoic acid (297 μL, 3.16 mmol) and 4-methylmorpholine (790 μL, 7.18 mmol) in DCM (20 mL) at −15° C. and the reaction mixture was allowed to stir for 20 min. A solution of ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (0.5 g, 1.44 mmol) in DCM (20 mL) was added, and the reaction allowed to warm to RT and stirred for 18 h. The solvents were removed in vacuo, and the mixture was partitioned between DCM (30 mL) and 1 M HCl (aq.) (10 mL), the organic layer was separated and washed with sat. NaHCO3 (aq.) (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (40 g, 50-70% EtOAc in isohexane) to afford 2-(dimethylcarbamoyl)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(3-methoxypropanoate) (UL1-104) (300 mg, 39%) as a yellow oil: m/z 521 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.24-7.15 (m, 2H), 6.98-6.89 (m, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.79 (s, 3H), 3.65-3.59 (m, 4H), 3.27 (s, 3H), 3.25 (s, 3H), 2.82 (s, 3H), 2.78 (t, J=6.0 Hz, 4H), 2.71 (s, 3H), 1.05 (t, J=7.1 Hz, 3H).

Provenance & Evidence