Lithium Hydroxide → (S)-3-(1-methyl-1H-imidazol-5-yl)-3-(4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methoxy)phenyl)propanoic acid

Participants

Reaction Steps

A mixture of 74.5 (0.15 mmol), 6-(bromomethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (0.18 mmol) and cesium carbonate (0.2 mmol) in DMF (2 mL), was stirred at room temperature for 16 hours. To the reaction mixture was added LiOH in water (1 mL, 1N solution), and the reaction was stirred at 50° C. for 3 hours. The mixture was filtered and purified by reverse phase HPLC to give 74 (35 mg, 0.08 mmol) after lyophilization. MS ESI (pos.) m/e 447.3 (M+H). 1H NMR (500 MHz) (CDCl3) δ 8.64 (1H, s), 7.59 (1H, s), 7.33-7.36 (2H, m), 7.20 (1H, dd, J=7.9, 1.8 Hz), 7.08 (2H, d, J=8.5 Hz), 6.98 (2H, d, J=8.5 Hz), 4.98 (2 H, s), 4.53 (1H, m), 3.57 (3H, s), 2.96-3.06 (2H, m), 1.71 (4H, s), 1.31 (6H, s), 1.30 (6H, s).

Provenance & Evidence