Water → 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid

Participants

Reaction Steps

Methyl 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 7) (304 mg, 0.71 mmol) was dissolved in THF (6 mL) and methanol (2 mL); 1 N lithium hydroxide solution (0.85 mL) was added followed by water (8 mL), and the resultant solution was stirred for 1 hr at room temperature. The majority of the organic solvent was removed by distillation, the remaining aqueous solution was filtered and acidified with 2N hydrochloric acid and extracted with 1:1 ethyl acetate: DCM (2×40 mL). The combined organic extracts were washed with water (10 mL) and brine (20 mL) and dried (MgSO4) to afford the product (265 mg, 96%). 1H NMR δ (300 MHz, CDCl3) 2.12-2.27 (m, 1H), 2.38 (quintet, 2H), 2.52-2.67 (m, 1H), 2.95 (s, 3H), 3.36-3.57 (m, 2H), 4.27 (t, 2H), 4.68 (t, 2H), 4.97 (t, 1H), 7.10 (s, 1H), 7.45 (s, 1H), 7.62 (s, 1H), 8.31 (s, 1H), 8.84 (s, 1H); m/z 413 (M+H)+

Provenance & Evidence