Reaction Steps
To a solution of 1-(2-chloroallyl)cyclopentanecarboxylic acid (80 mg, 0.42 mmol) in CH2Cl2 (3 mL) and DMF (3 mL) with (S)-2-amino-3-(biphenyl-4-yl)-N-(furan-2-ylmethyl)-N-methylpropanamide TFA salt (199 mg, 0.59 mmol) was added TEA (0.41 mL, 2.97 mmol) and HATU (161 mg, 0.42 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was quenched with aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with water (seven times), brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography using 10% EtOAc/heptane to 100% EtOAc/heptane to give (S)—N-(3-(biphenyl-4-yl)-1-((furan-2-ylmethyl)(methyl)amino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (151 mg). HPLC retention time=1.89 minutes (condition B); MS (m+1)=505.3. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.61-1.80 (m, 12H), 1.96-2.19 (m, 4H), 2.54-2.83 (m, 6H), 2.74 (s, 3H, major rotamer), 2.95 (s, 3H, minor rotamer), 2.01-3.13 (m, 2H), 4.23 (d, J=16.7 Hz, 1H, minor rotamer), 4.28 (d, J=15.2 Hz, 1H, major rotamer), 4.44 (d, J=16.7 Hz, 1H, minor rotamer), 4.77 (d, J=15.2 Hz, 1H, major rotamer), 5.06 (s, 1H, minor rotamer), 5.12 (d, J=1.3 Hz, 1H, major rotamer), 5.15 (d, J=1.3 Hz, 1H, minor rotamer), 5.19 (d, J=1.3 Hz, 1H, major rotamer), 5.17-5.28 (m, 1H, major rotamer), 5.39 (q, J=7.2 Hz, 1H, minor rotamer), 6.17 (d, J=2.8 Hz, 1H, minor rotamer), 6.24 (d, J=3.3 Hz, 1H, major rotamer), 6.30 (dd, J=3.3, 1.8 Hz, 1H, minor rotamer), 6.37 (dd, J=3.2, 1.9 Hz, 1H, major rotamer), 6.57 (d, J=8.1 Hz, 1H, minor rotamer), 6.68 (d, J=7.8 Hz, 1H, major rotamer), 7.21-7.65 (m, 18H).
