HCID 117642415, compound → HCID 89625023, compound

Participants

Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-(methylsulfonyl)propoxy)phenyl)-1H-pyrrole-2-carboxylate (44) (95 mg, 0.15 mmol) in MeOH (4 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 40° C. under H2 (full H2 mode). The output was concentrated in vacuo, and the compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 15-40% MeCN in 0.1% aq. formic acid over 16 min) to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-(methylsulfonyl)propoxy)phenyl)-1H-pyrrole-2-carboxylate (UL1-110) (40 mg, 58%) as a yellow solid: m/z 455 (M+H)+ (ES+); 453 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.58 (s, 1H), 8.45 (s, 1H), 7.07-7.02 (m, 2H), 6.89-6.84 (m, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.99 (q, J=7.1 Hz, 2H), 3.29-3.25 (m, 2H), 3.02 (s, 3H), 2.92-2.71 (br s, 6H), 2.21-2.07 (m, 2H), 0.99 (t, J=7.1 Hz, 3H).

Provenance & Evidence