HCID 86761247, compound → HCID 57877635, compound

Participants

Reaction Steps

((2R)-1-{[1-(3-Ethoxyphenyl)-2-(4-methylphenyl-1H-imidazol-4-yl]carbonyl}piperazin-2-yl)methyl acetate To 350 mg (0.330 mmol) of 10% palladium on carbon was added a solution of 3.55 g (5.95 mmol) of benzyl (3R)-3-[(acetyloxy)methyl]-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1-carboxylate from Step C in 50 mL of anhydrous methanol. The resulting suspension was agitated under an atmosphere of hydrogen at 40 psi for 2 hours then filtered through a plug of Celite®. The plug was washed with methanol (75 mL), and the combined filtrates were concentrated in vacuo to yield the title compound as a colorless foam, which was used without further purification. 1H NMR (DMSO-d6): δ 7.85 (s, 1 H), 7.33 (t, J=8.2 Hz, 1 H), 7.21 (d, J=8.5 Hz, 2 H), 7.13 (d, J=8.5 Hz, 2 H), 6.98-7.00 (m, 1 H), 6.92 (s, 1 H), 6.77-6.79 (m, 1 H), 4.68-5.81 (m, 2 H), 4.18-4.59 (m, 3 H), 4.00 (q, J=6.8 Hz, 2 H), 2.72-3.02 (m, 4 H), 2.57-2.62 (m, 1 H), 2.27 (s, 3 H), 1.78-2.00 (m, 3 H), 1.27 (t, J=6.8 Hz, 3 H). LC/MS 463.5 (M+1).

Provenance & Evidence