Hydrochloric Acid → (3S)-3-(4-(((5-(4-butylphenyl)-2-thienyl)methyl)oxy)phenyl)-3-(3-isoxazolyl)propanoic acid

Temperature

0 °C

To a solution of 60.6 (26 mg, 0.042 mmol) in THF (0.4 mL) were added 30% H2O2 (47 μL, 0.42 mmol) and 1N LiOH (0.21 mL, 0.21 mmol) at 0° C. The mixture was stirred for 1 h at 0° C., adjusted to pH 3 with aqueous HCl, and extracted with EtOAc. The combined organics were washed with 1N Na2SO3 (pH 3) and brine, dried (Na2SO4), and concentrated. The crude product was chromatographed on silica gel (10-45% EtOAc/hexane) and further purified by preparative thin layer chromatography (50% EtOAc/hexane) to afford 60 (1.6 mg, 8%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.28 (d, 1H), 7.48 (d, 2H), 7.18 (m, 4H), 7.14 (d, 1H), 7.04 (d, 1H), 6.94 (d, 2H), 6.07 (d, 1H), 5.17 (s, 2H), 4.55 (t, 1H), 3.35 (dd, 1H), 2.98 (dd, 1H), 2.61 (t, 2H), 1.60 (m, 2H), 1.37 (m, 2H), 0.93 (t, 2H).

1. extractionextracted with EtOAc
2. washThe combined organics were washed with 1N Na2SO3 (pH 3) and brine
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated
5. customThe crude product was chromatographed on silica gel (10-45% EtOAc/hexane)
6. customfurther purified by preparative thin layer chromatography (50% EtOAc/hexane)

ORD record

ord-f9b057fe745c42bd9e618d219e8f39e5

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2