HCID 71598927, compound → HCID 136252910, compound

Participants

Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylate (UL1-090) (85 mg, 0.16 mmol) in MeOH (6 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. The crude material was dissolved in DCM (5 mL) and washed with 1M HCl (aq.), brine (5 mL), sat. NaHCO3 (aq.) (5 mL), the basic aqueous layer was acidified with 1M HCl (aq.) (5 mL) and washed with DCM (2×5 mL), the combined organics were dried (MgSO4), filtered and solvents removed in vacuo to afford ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(2H-tetrazol-5-yl)-1H-pyrrole-2-carboxylate (UL1-089) (45 mg, 79%) as a white solid: m/z 346 (M+H)+ (ES+); 344 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.30 (br s, 1H), 8.67 (s, 1H), 7.10-7.05 (m, 2H), 6.87-6.81 (m, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.76 (s, 3H), 0.99 (t, J=7.1 Hz, 3H).

Provenance & Evidence