Sodium Hydroxide → (2S)-3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acid

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Reaction Steps

The title compound was prepared as follows: 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acid ethyl ester (0.017 g, 0.037 mmol) was dissolved in 0.25 M ethanolic NaOH solution (0.3 mL, 0.075 mmol). The mixture was stirred 16 hours at room temperature and water was added. The aqueous layer was extracted with Et2O (3×5 mL). The aqueous layer was acidified to pH=1 with 1 N HCl and extracted with Et2O (5×10 mL). The organic layer was dried (MgSO4) and concentrated under vacuum to give the title compound as a yellow oil (0.006 mg, 38%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.25 (m, 9H), 7.0–6.86 (m, 3H), 4.23 (q, 4H, J=6.18), 3.96 (dd, 1H, J=7.24, 4.28), 3.40 (s, 3H), 3.06 (dd, 1H, J=14.5, 4.28), 2.92 (dd, 1H, J=14.5, 7.24), 2.32 (qn, 2H, J=5.92).

Provenance & Evidence