Hydrochloric Acid → 5-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoic acid

Participants

Reaction Conditions

Reaction Steps

To the solution of methyl 5-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoate (367 mg, 0.68 mmol) in THF (13 mL) at 0° C. was added dropwise 1N aq KOH (3.42 mL, 5 eq). The reaction was stirred at 0° C. for 20 minutes and then at RT for 4 hours. It was then cooled back to 0° C. and 2N aq HCl was dropwise added to adjust the pH to about 5-6. The mixture was then evaporated at RT to remove the most of the THF. The oily residue was then partitioned between aq NH4Cl and CHCl3. The chloroform layer was isolated, followed by a wash with brine (1×) and then dried with anhydrous Na2SO4 overnight. The upper clear solution was decanted, concentrated, and subject to a gradient column chromatography (MeOH-DCM 1:500 to 1:9). The corresponding product fractions were collected, concentrated, and treated with EtOAc with stirring. The title compound was obtained upon filtration as white solid (238 mg, 67%).

Provenance & Evidence