Potassium Phosphate, Tribasic → HCID 86619683, compound

Participants

Reaction Conditions

Reaction Steps

Compound 35.4 (1.60 g, 3.40 mmol), 36.3 (0.91 g, 4.10 mmol), Pd(OAc)2 (0.11 g, 0.51 mmol), S-phos (0.42 g, 1.02 mmol) and K3PO4 were added to a flask. The flask was flushed with nitrogen and charged with dioxane (9.0 mL) and water (3.0 mL). The mixture was then stirred at 80° C. overnight. The solvent was removed, and the residue was purified by column chromatography to give an intermediate, (S)-ethyl 3-(4-(4-(5,5-dimethylcyclopent-1-enyl)-3-(trifluoromethoxy)benzyloxy)-phenyl)-3-(isoxazol-3-yl)propanoate (0.45 g, 0.85 mmol) that was treated with LiOH (1.0 mL, 3.33 M in water) in MeOH (6.0 mL) at room temperature overnight. The reaction mixture was purified by preparative HPLC (reverse phase) to give the title compound 36. 1H NMR (CD3CN) δ 1.04 (s, 6H), 1.85 (m, 2H), 2.41 (m, 2H), 2.97 (dd, J=7.5, 16.4 Hz, 1H), 3.17 (dd, J=7.5, 16.4 Hz, 1H), 4.52 (m, 1H), 5.07 (s, 2H), 5.26 (m, 1H), 6.23 (d, J=1.5 Hz, 1H), 6.94 (d, J=6.6 Hz, 2H), 7.22 (d, J=6.6 Hz, 2H), 7.35-7.39 (m, 3H), 8.41, (d, J=1.5 Hz, 1H). MS ESI (pos.) m/e: 502 (M+H).

Provenance & Evidence