To a solution of 90 mg (0.29 mmol) of (S)-2-amino-3-(3,4-dimethoxy-phenyl)-(tetrahydropyran-4-yl)-propionamide and 98 mg (0.29 mmol) of (S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carboxylic acid in 2 ml of dichloromethane was added 25 mg (0.29 mmol) of sodium bicarbonate followed by 40 mg (0.29 mmol) of HOAT and 56 mg (0.29 mmol) of EDCI. The mixture was stirred at room temperature for 17 hours after which it was purified by flash chromatography on silica gel, eluting with 50-100% ethyl acetate/heptane to give 0.162 g (0.25 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.00-1.40 (m, 7H); 1.84 (b, 2H); 2.12 (bd, 1H); 2.60 (t, 1H); 2.99 (dd, 1H); 3.18 (dd, 1H); 3.45 (t, 2H); 3.61 (bd, 1H); 3.79-4.00 (m, 9H); 4.38 (b, 1H); 4.62 (q, 1H); 5.96 (d, 1H); 6.74-6.83 (m, 4H); 7.70 (t, 1H); 7.87 (d, 1H); 8.00 (d, 1H); 8.07 (s, 1H).
