Triethylamine → HCID 25112583, compound

Participants

Reaction Steps

To a stirred and cooled (0° C.) mixture of [(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)-cyclopentyl-N—BOC-amino]-acetic acid (10 g, 30.5 mmol) and 1-hydroxybenzotriazole (5 g, 36.9 mmol) in dichloromethane (200 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.1 g, 36.9 mmol) in portions and the mixture was stirred for 0.5 h at the same temperature to result a clear solution. A solution of (2S,4S)-4-fluoropyrrolidine-2-carboxamide p-toluenesulfonate (5.71 g, 33.9 mmol) and triethylamine (6.4 ml, 4.62 mmol) in dichloromethane (60 ml) was added and the mixture was stirred for 3 h at room temperature. The reaction mixture was diluted with DCM (100 ml) and water (200 ml) and the layers were separated. The organic layer was washed with 0.5N HCl (100 ml) and then with brine (50 ml). The solvent was evaporated under reduced pressure to give 10 g of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.25-1.33 (m, 2H), 1.42 (s, 9H), 1.70-1.99 (m, 5H), 2.04-2.47 (m, 2H), 2.80-2.82 (m, 1H), 3.63-3.91 (m, 4H), 4.14-4.17 (m, 2H), 4.35-4.37 (m, 2H), 4.74 (d, J=9.6 Hz, 1H), 5.25-5.42 (m, 1H), 7.93 (s, 1H), 8.06 (s, 0.6H, rotomer), 8.08 (s, 0.4H, rotomer).

Provenance & Evidence