Hydrochloric Acid → HCID 57929459, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide (1.8 M in toluene, 26.6 mL) was added, dropwise, at −78° C., to a solution of EtOAc (2.33 mL, 23.92 mmol) in THF (100 mL), and the resulting mixture was stirred at −78° C. for 1 h. A solution of benzotriazol-1-yl-(4-cyclopentylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanone (7.698 g, 21.74 mmol) in THF (60 mL) was added via cannula to the reaction mixture, and the resulting mixture was stirred at −78° C. for 4 h and at RT for 15 h. The reaction mixture was then treated with HCl (1 M aq) and then with HCl (6 M aq) until pH 2. The resulting mixture was stirred at RT for 1 h, was then diluted with EtOAc. The organic layer was separated and washed 3 times with water; the aqueous layers were combined and extracted 3 times with EtOAc and 3 times with a mixture of isopropanol and chloroform (1:1). The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (heptane/EtOAc, 100/0 to 80/20) to give 3.03 g (42% yield) of 3-(4-cyclopentylamino-2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester.

Provenance & Evidence