Hydrochloric Acid → HCID 54748165, compound

Participants

Reaction Steps

To a stirred solution of (7S,10R)-10-[[(dimethylamino)(oxo)acetyl](ethyl)amino]-2-{[(4-fluorobenzyl)amino]carbonyl}-7-methoxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-3-yl methanesulfonate (1 g, 1.72 mmol) in 2-propanol (17 mL) was added 2M NaOH (2.58 mL, 5.16 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes, quenched with HCl (1M, 5.16 mL, 5.16 mmol), and extracted with EtOAc (3×). Three additional reactions on the same scale were performed in parallel. The combined organic layers from all four reactions were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (C18 Sunfire column) using a water/acetonitrile mobile phase gradient containing 0.5% TFA or by precipitation from water to provide N-ethyl-N-((7S,10R)-2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-7-methoxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)-N′,N′-dimethylethanediamide. LC-MS: 504.5 (M+1).

Provenance & Evidence