Hydrochloric Acid → trans-4-(N,N-Dimethylglycylamino)-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

Participants

Reaction Steps

N-tert-Butoxycarbonyl-trans-4-(N,N-dimethylglycylamino)-L-prolyl-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (C, 76 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (10 mL) at 0° C., and stirred at 0†° C. for 5 min and at room temperature for 3 hr. The solution was evaporated in vacuo, and the residue was purified by HPLC (Shiseido, Capeell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid:methanol=55:45, v/v) and freeze-dried from water to afford the title compound (28 mg) as a pale yellow powder: 1H NMR (400 MHz, D2O) δ 1.83-2.07 (m, 2H), 2.22-2.47 (m, 3H), 2.47-2.68 (m, 3H), 2.81 (s, 6H), 3.26-3.39 (m, 1H), 3.52-3.70 (m, 2H), 3.80-3.98 (m, 3H), 4.00-4.08 (m, 1), 4.31-4.52 (m, 2H), 4.68-4.84 (m, 2H), 7.07-7.29 (m, 5H), 7.73-7.81 (m, 1H),7.86-7.95 (m, 1H), 7.99-8.12 (m, 2H), 8.87 (s, 1H), and 9.21 (s, 1H); IR (KBr) 3367, 3025, 2952, 1654, 1648, 1610, 1571, 1554, and 1454 cm−1; mass spectrum (FAB+) m/e 616 (M+1); high-resolution mass (FAB) m/e Calcd for C33H41 N7O5: 616.3247. Found: 616.3237.

Provenance & Evidence