Lithium Hydroxide → (S)-3-(4-((2-(4-Butylphenyl)-4-methylthiazol-5-yl)methoxy)phenyl)-3-(4,5-dihydroisoxazol-3-yl)propanoic acid

Participants

Reaction Steps

Cesium carbonate (64 mg, 0.2 mmol) was added to a mixture of 9.2 (6.1 mg, 0.015 mmol) and 2-(4-butylphenyl)-5-(chloromethyl)-4-methylthiazole hydrochloride (14.1) (6 mg, 0.018 mmol) in DMSO (0.5 mL). The mixture was stirred at room temperature for 3 hours. To the reaction mixture was added LiOH in water (0.5 mL, 1 N solution), and the mixture was stirred at 50° C. for 3 hours. The mixture was filtered and purified by reverse phase HPLC to give 14 (6 mg, 0.012 mmol) after lyophilization. MS ESI (pos.) m/e 479.2 (M+H). 1H NMR (500 MHz, CDCl3) δ ppm 7.84 (2 H, d, J=8.3 Hz), 7.32 (2 H, d, J=8.1 Hz), 7.25 (2 H, d, J=8.6 Hz), 6.97 (2 H, d, J=8.8 Hz), 5.20 (2 H, s), 4.31-4.35 (1 H, m), 4.23-4.29 (1 H, m), 4.10 (1 H, t, J=8.1 Hz), 3.28 (1 H, dd, J=16.4, 7.8 Hz), 2.82-2.90 (2 H, m), 2.73-2.77 (1 H, m), 2.69 (2 H, t, J=7.8 Hz), 2.53 (3 H, s), 1.62-1.68 (2 H, m), 1.36-1.42 (2 H, m), 0.96 (3 H, t, J=7.3 Hz)

Provenance & Evidence