Hydrochloric Acid → HCID 11259967, compound

Participants

Reaction Conditions

Reaction Steps

[(R)-4-(3-Biphenyl-4-yl-ureido)-5-phenyl-pentyl]-(2-pyrrolidin-1-yl-ethyl)-carbamic acid benzyl ester. To a solution of ((R)-4-tert-butoxycarbonylamino-5-phenyl-pentyl)-(2-pyrrolidin-1-yl-ethyl)-carbamic acid benzyl ester (0.06 g, 0.16 mmol) in CH2Cl2 (1.7 mL) was added HCl in dioxane (3 M, 0.6 mL), and the solution was stirred (25° C., 1 h). The solution was concentrated in vacuo, and the residue was dissolved in MeOH (2 mL) and treated with basic resin, and the resulting suspension was stirred (25° C., 1 h). The suspension was filtered and concentrated in vacuo, and the residue was dissolved in CH2Cl2 (2.0 mL). The solution was treated with 4-biphenylisocyanate (0.033 g, 0.17 mmol), and the reaction mixture was stirred for 4 h (25° C.), during which time a precipitate, the desired product, formed. The product was collected as a clear semi-solid (0.064 g, 64%). MS (electrospray): mass calculated for C38H44N4O3, 604.79; m/z found, 605.3 [M+H]+, 627.3 [M+Na]+. 1H NMR (CDCl3, 400 MHz): 7.09–7.49 (m, 21H), 5.01–5.04 (m, 2H), 3.41 (br s, 1H), 3.14–3.30 (m, 2H), 2.85–2.92 (m, 2H), 2.49–2.58 (m, 8H), 1.17–1.56 (m, 8H).

Provenance & Evidence