Hydrogen Peroxide → HCID 21051844, compound

Temperature

0 °C

A solution of 3-[2(R)-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-propionyl]-4(S)-isopropyl-oxazolidin-2-one (560 mg, 1.40 mmol) in tetrahydrofuran (30 mL) and water (10 mL) cooled to 0° C. was treated with a 30% aqueous hydrogen peroxide solution (0.7 mL) and lithium hydroxide (117 mg, 2.80 mmol). The reaction was stirred at 0° C. for 1 h. At this time, the reaction was quenched with an aqueous sodium sulfite solution (0.71 g, 5.6 mmol in 4 mL) followed by the addition of a 0.5N aqueous sodium bicarbonate solution (13 mL). The tetrahydrofuran was then removed in vacuo. The residue was diluted with water (60 mL) and extracted with methylene chloride (3×20 mL). The aqueous layer was then acidified to pH=2 with a 5N aqueous hydrochloric acid solution and then was extracted with ethyl acetate (4×25 mL). The combined organic layers were then dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2(R)-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid (203 mg, 48%) as clear colorless oil.

1. customThe tetrahydrofuran was then removed in vacuo
2. additionThe residue was diluted with water (60 mL)
3. extractionextracted with methylene chloride (3×20 mL)
4. extractionwas extracted with ethyl acetate (4×25 mL)
5. dry with materialThe combined organic layers were then dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-09ccf2e6238e429bb1891dce526be8b0

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2