4-Methylmorpholine → N-(cyanomethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide

関与物質

反応手順

(R/S)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-V, 50 mg, 0.116 mmol) was dissolved in DMF (1 mL) prior to the addition of 4-methylmorpholine (0.102 mL, 0.927 mmol), 2-aminoacetonitrile, HCl (13.94 mg, 0.151 mmol), and HATU (66.1 mg, 0.174 mmol). This was stirred overnight before EtOAc was added. The EtOAc solution was washed with 1N HCl, sat NaHCO3, and brine. The organic layer was then dried with MgSO4 and concentrated to give N-(cyanomethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (51 mg, 0.088 mmol, 76% yield): LCMS=470.2 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.15-8.23 (2 H, m), 7.65-7.76 (4 H, m), 7.53-7.64 (3 H, m), 5.21 (1 H, s), 4.19 (2 H, d, J=2.86 Hz). HPLC Peak RT=9.5 min (Analytical Method A).

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