Hydrochloric Acid → (+)-3-(5-cyanobenzo[d]oxazol-2-yl)-3-(5-methoxy-7-methyl-1H-indol-4-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

(±)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-3-methoxy-3-oxopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 148-A) (0.3 g, 0.613 mmol) was dissolved in MeOH (6 ml). cesium carbonate (0.998 g, 3.06 mmol) was added and the reaction was heated at 65° C. for 2.5 hours. The reaction was then cooled to room temperature and treated with 1 N HCl until pH=˜3. The mixture was then diluted with DCM and passed through a phase separator, concentrated and purified via preparative HPLC (HC-B) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.00 (br. s., 1H) 8.34 (t, J=1.14 Hz, 1H) 7.58-7.92 (m, 2H) 7.22 (t, J=2.78 Hz, 1H) 6.77 (s, 1H) 6.22 (dd, J=3.03, 1.89 Hz, 1H) 5.39 (dd, J=9.85, 4.67 Hz, 1H) 3.72 (s, 3H) 3.57 (dd, J=16.67, 9.98 Hz, 1H) 2.74 (dd, J=16.67, 4.67 Hz, 1H) 2.44 (d, J=0.63 Hz, 3H). HRMS calcd. for C21H17N3O4 (M+H)+ 376.1297. found 376.1290.

Provenance & Evidence