HCID 57595477, compound → HCID 57595476, compound

Participants

Reaction Steps

Benzyl 2-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)pyrrolidine-1-carboxylate (237 mg, 0.381 mmol) was dissolved in HBr/Acetic acid (5 mL) and stirred for 2 h. The reddish slurry was partitioned between Et2O and 1N HCl. The HCl/water layer was washed 3× with Et2O to rid the benzyl bromide. The water layer was neutralized with 1N NaOH, and washed 3× with methylene chloride. The organic layer was dried over MgSO4, filtered and concentrated to afford the title compound (170 mg, 91%) as a white solid. 1H-NMR (CDCl3) δ: 1.05-1.20 (m, 1H), 1.13 (s, 3H), 1.50-1.62 (m, 1H), 1.76-1.90 (m, 2H), 2.02 (s, 3H), 2.05-2.20 (m, 2H), 2.20-2.38 (m, 1H), 2.93-3.03 (m, 1H), 3.09-3.18 (m, 1H), 4.05 (t, 1H), 4.72-4.82 (m, 1H), 5.45-5.75 (m, 1H), 6.49 (d, 1H), 6.88 (t, 1H), 7.11-7.29 (m, 8H), 7.37 (d, 2H).

Provenance & Evidence