Hydrochloric Acid → HCID 71009647, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-acetyl-1-{2-[(1R,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hex-2-yl]-2-oxo-ethyl}-1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid methyl ester (Example 689, 70 mg, 0.133 mmol) in THF (3 mL) and water (0.3 mL) was added a 2N aqueous LiOH solution (0.664 mL, 1.33 mmol). The reaction mixture was stirred at 25° C. for 16 h, then a 1N HCl aqueous solution was added to acidify the reaction mixture to pH=2 to 3. The resulting aqueous suspension was filtered, the solid was washed with water and then dried in vacuo. The crude solid was purified by preparative HPLC (Waters Sunfire C18-OBD, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 20% to 100% CH3CN in H2O in 20 min, 100% CH3CN 2 min, CH3CN and H2O containing 0.1% TFA). The pure fractions were combined, CH3CN was evaporated under reduced pressure and the resulting aqueous solution was lyophilized to give the title compound as a white solid. MS: 513 [M+H]+, 535 [M+Na]+; tR (HPLC conditions k): 3.14 min.

Provenance & Evidence