Tetrahydrofuran → 4-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

The product from Step 1 (503 mg, 1.70 mmol, 1.00 equiv) was dissolved in 3/1 MeOH:THF (8 mL total). Following addition of 2.5N NaOH (2 mL), the reaction mixture was heated to 60° C. for 6 hours, then stirred at room temperature for an additional 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed again with 1N NaOH. The aqueous phases were combined and acidified to pH˜1 with 5N HCl, and extracted twice with ethyl acetate. The combined organic extracts were washed with satd. NaCl, dried over Na2SO4, and filtered. The filtrate was concentrated en vacuo and azeotroped several times with hexanes to afford 252 mg (52%) of the acid as an off-white solid. MS (ES+) m/e 284 [M+H]+.

Provenance & Evidence