Hydrochloric Acid → trans-4-Glycylamino-L-Proline 4-Benzylphenylamide Dihydrochloride

Participants

Reaction Steps

trans-4-(N-tert-Butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline 4-benzylphenylamide (A, 158 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (6 mL). After stirring for 2 hr, the reaction mixture was evaporated in vacuo to give white solids. The solids were washed with ether to afford the title compound (A, 103 mg): 1H NMR (400 MHz, D2O) δ 2.59 (dd, J=7.8, 6.4 Hz, 2H), 3.48 (dd, J=12.7, 4.8 Hz, 1H), 3.83 (dd, J=12.7, 6.4 Hz, 1H), 3.85 (s, 2H), 4.00 (s, 2H), 4.62 (m, 1H), 4.73 (m, 1H), and 7.28-7.42 (m, 9H).

Provenance & Evidence