Hydrochloric Acid → 2-(4-tert-Butylphenyl)-N-{(S)-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide

Participants

Reaction Steps

To a solution of ethyl(4-{(S)-{[(4-tert-butylphenyl)acetyl]amino}[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)acetate (0.190 g, 0.356 mmol) in 1.0 ml of anhydrous THF at RT was added 2.0N LiBH4 in THF (0.214 ml, 0.427 mmol). The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was quenched with 1.0N HCl (2.0 ml, 2.000 mmol), stirred for 30 min. and 2.0 N NaOH (2.0 ml, 4.000 mmol) was added. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 0.047 g (27%) of the title compound. ES-MS [M+1]+: 492.3. This intermediate was carried over to the next step without further purification and characterization.

Provenance & Evidence