1-(3-Methylphenyl)butane-1,3-dione → (2S)-2-{[(Z)-1-methyl-3-(3-methylphenyl)-3-oxo-1-propenyl]amino}-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid

Participants

Reaction Steps

The title compound was prepared (as described above for the preparation of Example 2) from 100 mg (0.27 mmol) of Intermediate 45 and 48 mg (0.27 mmol) of Intermediate 21 to yield 104 mg of Example 46. 1H NMR (DMSO-d6, 400 MHz) δ11.47 (d, 1H, J=9.06), 7.95 (m. 2H), 7.65 (m, 2H), 7.54 (m, 3H), 7.31 (m, 2H), 7.19 (d, 2H, J=8.51), 6.88 (d, 2H, J=8.51), 5.64 (s, 1H), 4.23 (m, 1H), 4.23 (m, 3H), 3.21 (m, 1H), 2.96 (m, 2H), 2.86 (m, 1H), 2.60 (s, 3H), 1.80 (s, 3H); low resolution MS (ES) m/e 525.2 (MH+); RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 50-100% CH3CN in H2O) with 0.1% HCO2H buffer 30 minutes; 1 mL/min: tf15.57 min (to=1.43).

Provenance & Evidence