HCID 10977715, compound → HCID 11085622, compound

BH3-THF complex (49 mL of a 1.0 M solution in THF) was added dropwise via addition funnel over 50 min to a solution of (5-methyl-2-phenethyl-oxazol-4-yl)-acetic acid (5.05 g, 20.6 mmol) in THF (35 mL). The reaction mixture was stirred at ambient temperature for 3 h, and then quenched with MeOH (12 mL). After heating at 50° C. for 2 h, the reaction mixture was cooled to ambient temperature, and then partitioned between CH2Cl2 and 1N NaOH. The organic phase was washed with brine (1×50 mL), dried over MgSO4 and concentrated to obtain a residue, which was purified by column chromatography (500 mL SiO2, 35% EtOAc/hexanes) to provide 3.99 g (84%) of the desired product as a clear, colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 3.84 (q, J=5.6 Hz, 2H), 3.06-2.67 (m, 4H), 2.62 (t, J=5.6 Hz, 2H), 2.22 (s, 3H); MS (EI+) 232.19 (M+H); 254.15 (M+H+Na).

1. customquenched with MeOH (12 mL)
2. temperatureAfter heating at 50° C. for 2 h
3. temperaturethe reaction mixture was cooled to ambient temperature
4. custompartitioned between CH2Cl2 and 1N NaOH
5. washThe organic phase was washed with brine (1×50 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customto obtain a residue, which
9. customwas purified by column chromatography (500 mL SiO2, 35% EtOAc/hexanes)

ORD record

ord-875b6ab81bec42df9f169ee26dd4ccdd

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07282501B2