Hydrochloric Acid → HCID 11751765, compound

Participants

Reaction Steps

To a solution of [(S)-2-phenyl-1-(3-pyrrolidin-1-yl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (Example 1, step A) (0.083 g, 0.22 mmol) in CH2Cl2 (3 mL), a 4 M solution of HCl in dioxane (0.55 mL, 2.2 mmol) was added, and the mixture was stirred for 3 h at rt. The solvents were removed. The residue was treated with CH2Cl2, and the solvent was removed again under reduced pressure. The residue was dissolved in CH2Cl2 (3 mL), and at 0° C., TEA (0.56 g, 0.55 mmol) was added followed by 4-isocyanato-biphenyl (0.052 g, 0.264 mmol). The mixture was warmed to rt over a period of 2 h and was then diluted with EtOAc (100 mL). The organic layer was washed with saturated NaHCO3 (25 mL) and brine (25 mL), and was dried (Na2SO4). The solvent was removed, and the residue was purified by flash column chromatography using 0–20% MeOH (1% NH4OH)/CH2Cl2 to afford 0.08 g (77%) of the desired product. MS (electrospray): mass calculated for C29H34N4O2, 470.27; m/z found, 471.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.56–7.48 (m, 4H), 7.42–7.36 (m, 4H), 7.33–7.22 (m, 6H), 4.47 (t, J=7.1 Hz, 1H), 3.20–3.16 (m, 2H), 3.07 (dd, J=13.6, 7.1 Hz, 1H), 2.99 (dd, J=13.6, 7.1 Hz 1H), 2.51 (br m, 4H), 2.42 (m, 2H), 1.77 (br m, 4H), 1.65 (m, 2H).

Provenance & Evidence