Trifluoroacetic acid → HCID 59402458, compound

Participants

Reaction Steps

Ethyl-(3S,4R)-4-[(tert-butoxycarbonyl)amino]-3-(propyoxypiperidine-1-carboxylate (Intermediate 72, 3 g) was treated with TFA (5 mL) for 30 min and the concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (150 mL) with 4-chloro-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 27, 1.45 g, 9.13 mmol), HOBT (1.676 g, 10.95 mmol) and N-methyl morpholine (2.76 g, 27.39 mmol). The reaction mixture was stirred for 1 h at room temperature and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.02 g, 16.43 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 2N hydrochloric acid (30 mL) and the layers were separated. The organic layer was washed with sodium bicarbonate (40 mL), water (60 mL) and finally with brine successively and dried over anhydrous sodium sulphate, filtered, and concentrated under vacuum to afford ethyl (3S,4R)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-propoxypiperidine-1-carboxylate 2.8 g (84%) as solid.

Provenance & Evidence