Hydrochloric Acid → HCID 21341591, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4 N hydrogen chloride in 1,4-dioxane (10 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-prolyl-D-homophenylalanine 3-quinolylamide (C, 162 mg) in methanol (10 mL) at 0° C. After stirring at 0° C. for 5 min and at room temperature for 3 hr, the solution was concentrated in vacuo. The residue was purified by HPLC(Shiseido, Capcell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid: methanol=65:35, v/v) and freeze-dried from water to afford the title compound (90 mg) as a pale yellow powder: 1H NMR (400 MHz, D2O) δ 2.18-2.43 (m, 3H), 2.43-2.57 (m, 1H), 2.74-2.96 (m, 2H), 3.40 (dd, J=12.2,4.4 Hz, 1H), 3.76-3.87 (m, 3H), 4.45-4.60 (m, 2H), 4.61-4.73 (m, 1H), 7.01-7.17 (m, 1H), 7.17-7.31 (m, 4H), 7.86 (t, J=7.8 Hz, 1H), 8.00 (t, J=7.8 Hz, 1H), 8.04-8.19 (m, 2H), 8.81 (s, 1H), and 9.15 (s, 1H); IR (KBr) 3388, 3205, 3037, 1685, 1681, 1610, 1571, 1552, 1496, 1486, and 1454 cm−1; mass spectrum (EI+) m/e 474 (M+); (FAB+) m/e 475 (M+1); Anal. Calcd for 26H30N6O3.3HCl.3H2O: C, 48.95; H, 6.16; N, 13.17. Found: C, 49.16; H, 5.90; N, 13.15.

Provenance & Evidence