Hydrochloric Acid → 1-(Piperazin-2-ylcarbonyl)-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

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Reaction Steps

A solution of 4 N hydrochloric acid in 1,4-dioxane (5 mL) was added to 1,4-di-(N-tert-butoxycarbonyl)piperazin-2-ylcarbonyl)-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (C, 76 mg) at 0° C., and methanol (2 mL) was added to dissolve insoluble materials. After stirring for 1.5 hr, the reaction mixture was evaporated and coevaporated three times with 1,4-dioxane and ether in vacuo to give pale yellow solids. The solids were washed with ether to afford the title compound (64 mg) as a colorless solid: 1H NMR (400 MHz, D2O) δ 1.92-2.05 (m, 2H), 2.34-2.48 (m, 1H), 2.67(t, 2H), 3.24-4.89 (m, 13H), 7.15-7.32 (m, 5H), 7.83 (t, 1H), 7.96 (t, 1H), 8.09-8.16 (m, 2H), 8.94 (d, 1H), and 9.27 (d, 1H); mass spectrum (FAB+) m/e 531 (M+1); Anal. Calcd. for C29H34N6O4.3HCl.3H2O: C, 50.06; H, 6.26; N, 12.08. Found: C, 50.56; H, 6.34; N, 1.48.

Provenance & Evidence