Trifluoroacetic acid → HCID 86753679, compound

Participants

Reaction Steps

To the obtained N-(N-Boc-βethyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid ethyl ester (0.38 g, 0.95 mmol) were added anisole (0.3 ml) and TFA (10 ml) and the mixture was stirred for 1 hour under cooling with ice. After the TFA was distilled off at room temperature, the residue was washed with hexane 3 times and dissolved in DMF (20 ml) under cooling with ice. After the resulting solution was neutralized with triethylamine, 4-(4-morpholinoimidoyl)benzoic acid (0.25 g, 1.05 mmol), HOBT (0.14 g, 1.05 mmol) and WSDC (0.22 g, 1.14 mmol) were added thereto and the mixture was stirred overnight. After the solvent was distilled off, the residue was dissolved in ethyl acetate, washed sequentially with a 5% aqueous solution of citric acid, a 5% aqueous solution of sodium hydrogencarbonate and saturated saline 3 times each, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was applied to a silica gel column (2.1 φ×20 cm) and eluted with a mixed solution (chloroform:ethanol=30:1). The desired fractions were collected and the solvents were distilled off to yield a powder of the titled compound (108 mg, 22%).

Provenance & Evidence