4-[(4-Methoxyphenyl)methoxy]aniline → Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-((4-methoxybenzyl)oxy)phenyl)-1H-pyrrole-2-carboxylate (35) [prepared using the same procedure as Example B except 4-((4-methoxybenzyl)oxy)aniline used in step (i)] (46 mg, 0.07 mmol) in AcOH (5 mL) was stirred at 105° C. for 18 h. The volatiles were removed in vacuo and the residue was purified by silica gel chromatography (4 g, 0-10% MeOH in DCM) to afford ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (36) (35 mg, 91%) as a yellow solid: m/z 515 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 9.63 (1H, s), 7.47-7.42 (m, 2H), 7.41-7.29 (m, 8H), 6.99-6.91 (m, 2H), 6.73-6.66 (m, 2H), 5.10 (s, 2H), 4.95 (s, 2H), 3.99 (q, J=7.1 Hz, 2H), 2.69 (s, 3H), 2.67 (s, 3H), 1.00 (t, J=7.1 Hz, 3H).

Provenance & Evidence