1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11699940, compound

Participants

Reaction Steps

To a solution of 0.094 g (0.94 mmol) of 4-aminotetrahydropyran and 0.48 g (0.94 mmol) of (S)-3-(4-methoxy-phenyl)-2-{[(S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-propionic acid in 50 ml of dichloromethane was added 0.079 g (0.94 mmol) of sodium bicarbonate followed by 0.128 g (0.94 mmol) of HOAT and 0.179 g (0.94 mmol) of EDCI. The mixture was stirred at room temperature for 17 hours after which it was washed with brine and purified by flash chromatography on silica gel, eluting with 50-100% ethyl acetate/heptane to give 0.50 g (0.83 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.00-1.21 (m, 3H); 1.32-1.43 (m, 4H); 1.80 (b, 2H); 2.14 (bd, 1H); 2.69 (t, 1H); 2.99 (dd, 1H); 3.13 (dd, 1H); 3.45 (s, 2H); 3.65 (bd, 1H); 3.78 (s, 3H); 3.87-4.00 (m, 3H); 4.39 (b, 1H); 4.58 (q, 1H); 5.88 (d, 1H); 6.78 (d, 1H); 6.85 (d, 2H); 7.13 (d, 2H); 7.70 (t, 1H); 7.88 (d, 1H); 8.00 (d, 1H); 8.08 (s, 1H).

Provenance & Evidence