3-Fluorobenzoic Acid → HCID 89466085, compound

Participants

Reaction Steps

To a solution of Example 96B (100 mg, 0.349 mmol), 3-fluorobenzoic acid (58.7 mg, 0.419 mmol) and hydroxybenzotriazole (58.8 mg, 0.384 mmol) in dichloromethane (1.5 mL), was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.067 mL, 0.384 mmol). The mixture was stirred at room temperature overnight. The mixture was then purified via HPLC (Gilson®, XBridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=250 nm) to give the title compound as the first eluting diastereomer. 1H NMR (500 MHz, methanol-d4) δ ppm 1.74-1.81 (m, 1 H), 2.19-2.25 (m, 1 H), 2.34 (td, 1H, J=11, 3 Hz), 2.38-2.44 (m, 1 H), 2.49 (m, 1H), 2.83 (dd, 1H, J=12, 10 Hz), 2.98-3.06 (m, 1 H), 3.08-3.18 (m, 2 H), 4.31-4.40 (m, 2 H), 4.51-4.57 (m, 1 H), 6.96 (d, 1H, J=7 Hz), 6.99 (d, 1H, J=8 Hz), 7.29 (td, 1H, J=8, 1 Hz), 7.49 (td, 1H, J=8, 6 Hz), 7.59 (dt, 1H, J=9, 2 Hz), 7.63-7.70 (m, 2 H); MS (DCI) m/z 409 (M+H)+.

Provenance & Evidence