Hydrochloric Acid → (S)-3-(4-(3-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

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Reaction Steps

To a solution of the oxazolidinone (34.4) (8.9 mg, 0.013 mmol) dissolved in THF (0.5 mL), was added a 30% hydrogen peroxide solution (15.0 μL, 0.130 mmol) followed by a 2 M LiOH solution (33.0 μL, 0.065 mmol). The resulting slurry was stirred for two hours. The reaction mixture was diluted with water and acidified with hydrochloric acid to a pH ˜3. The mixture was then extracted with EtOAc (3×10 mL), and the organic layer was washed with an acidic sodium sulfite solution (1×5 mL) and brine (1×5 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 34 (2.60 mg). MS ESI (pos.): m/e 505.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.33 (1H, d, J=1.6 Hz), 7.40 (1H, s), 7.20-7.34 (3H, m), 7.13 (2H, d), 6.86 (2H, d, J=9.0 Hz), 6.16 (1H, d, J=1.6 Hz), 6.03 (1H, br. s.), 4.99 (2H, s), 4.44 (1H, t, J=7.8 Hz), 3.90-3.98 (2H, m, J=2.7 Hz), 3.50 (2H, t, J=5.7 Hz), 3.09 (1H, dd, J=16.4, 8.2 Hz), 2.84 (1H, dd, J=16.4, 7.4 Hz), 2.37-2.45 (2H, m, J=2.0 Hz), 1.37 (9H, s).

Provenance & Evidence