Hydrogen Peroxide → HCID 18739625, compound

Temperature

25 °C

A solution of 3-{2(R)-biphenyl-4-yl-3-cyclopentyl-propionyl}-4(S)-isopropyl-oxazolidin-2-one (127.4 mg, 0.31 mmol) in tetrahydrofuran (1.3 ml,) and water (300 μL) was cooled to 0° C. and then sequentially treated with a 30% aqueous hydrogen peroxide solution (39 μL, 1.25 mmol ) and an 0.8M aqueous lithium hydroxide solution (628 μL, 0.50 mmol). The reaction mixture was allowed to warm to 25° C. where it was stirred for 7 h. At this time, the reaction mixture was treated with solution of sodium sulfite (158.4 mg, 1.26 mmol) in water (952 μL). The reaction mixture was stirred at 0° C. for 30 min and then concentrated in vacuo to remove tetrahydrofuran. The resulting aqueous layer was extracted with diethyl ether (1×100 mL). The aqueous layer was then acidified to pH=1 with a 10% aqueous hydrochloric acid solution and extracted with ethyl acetate (1×100 mL). The organic extract was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 2(R)-biphenyl-4-yl-3-cyclopentylpropionic acid (43 mg, 46%) as a white solid: mp 136-137° C.; EI-HRMS m/e calcd for C20H22O2 (M+) 294.1620, found 294.1618.

1. stirringThe reaction mixture was stirred at 0° C. for 30 min
2. concentrationconcentrated in vacuo
3. customto remove tetrahydrofuran
4. extractionThe resulting aqueous layer was extracted with diethyl ether (1×100 mL)
5. extractionextracted with ethyl acetate (1×100 mL)
6. extractionThe organic extract
7. washwas washed with water
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-435e62620b4b48e58c4407280811e6ad

Source dataset

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06384220B2