4-Methylmorpholine → HCID 53496466, compound

Participants

Reaction Steps

(R/S)-3-(2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)propanoic acid (Int-V, 25 mg, 0.050 mmol), 4-methylmorpholine (20.13 mg, 0.199 mmol), 3-methylazetidin-3-ol, HCl (6.15 mg, 0.050 mmol), and HATU (24.60 mg, 0.065 mmol) were added to DMF (1 mL). This was stirred for 1 h before it was purified by prep HPLC (Sun Fire C18 5u19×100 mm, gradient elution with Method 1—MeOH/water containing 0.1% trifluoroacetic acid as defined above, 0% B to 100% B over 10 min, 20 mL/min, 220 nM, product retention=11.3 min) to provide (R/S)-2-hydroxy-N-(3-(3-hydroxy-3-methylazetidin-1-yl)-3-oxopropyl)-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (9 mg, 0.014 mmol, 27.8% yield): LCMS=572.3 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.16-8.20 (2 H, m), 7.54-7.74 (7 H, m), 5.11 (1 H, s), 3.96-4.04 (2 H, m), 3.81-3.87 (2 H, m), 3.47-3.52 (2 H, m), 2.36-2.43 (2 H, m), 1.44 (3 H, d, J=6.60 Hz); HPLC peak RT=8.3 min (Method A).

Provenance & Evidence