Ammonium Chloride → HCID 89610373, compound

Participants

Reaction Conditions

Reaction Steps

HATU (153 mg, 0.40 mmol) was added to a stirred solution 2-((4-(benzyloxy)-2,5-bis(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrol-3-yl)oxy)acetic acid (24) (100 mg, 0.20 mmol), DIPEA (176 μL, 1.00 mmol), and NH4Cl (53.8 mg, 1.00 mmol) in THF (2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 20 min and then at RT for 2 h volatiles were removed in vacuo, dissolved in EtOAc (30 mL) and washed with 1 M HCl (3×30 mL), sat. NaHCO3 (aq.) (3×30 mL) and brine (30 mL), dried (MgSO4), filtered and solvents removed in vacuo to give a yellow oil. The product was purified by silica gel chromatography (12 g, 0-100% EtOAc in isohexane) to afford diethyl 3-(2-amino-2-oxoethoxy)-4-(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (25) (66 mg, 66%) as a white solid: m/z 497 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.58 (br s, 1H), 7.51 (br s, 1H), 7.49-7.44 (m, 2H), 7.43-7.33 (m, 3H), 7.17-7.09 (m, 2H), 6.95-6.86 (m, 2H), 5.10 (s, 2H), 4.46 (s, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.98 (q, J=7.1 Hz, 2H), 3.79 (s, 3H), 0.97 (t, J=7.1 Hz, 3H), 0.96 (t, J=7.1 Hz, 3H).

Provenance & Evidence