4-Methylmorpholine → HCID 86680511, compound

Participants

Reaction Steps

To a solution of the product from Example 54F (0.05 g, 0.168 mmol) and 2-hydroxy-2-(3-(trifluoromethyl)phenyl)acetic acid (0.035 g, 0.160 mmol) in anhydrous N,N-dimethylformamide (1.5 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.070 g, 0.185 mmol) and N-methylmorpholine (0.056 mL, 0.505 mmol). The resulting mixture was stirred at room temperature for 90 minutes and was then partitioned between water and ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% methanol in dichloromethane. The title compound was obtained as a colorless solid (73 mg, 94%). 1H NMR (300 MHz, CDCl3) δ ppm 0.87-0.99 (m, 4 H) 1.23-3.25 (m, 9H) 3.48-3.73 (m, 2 H) 4.57-4.84 (m, 2 H) 5.20-5.37 (m, 2 H) 7.45-7.64 (m, 4 H) 7.87-8.05 (m, 2 H); MS (ESI) m/z 463 (M+H)+.

Provenance & Evidence