Hydrochloric Acid → (2R,3R)-2-Styryl-tetrahydro-pyran-3-carboxylic acid

To a stirring solution of (4R)-4-benzyl-3-[(2R,3R)-2-styryl-tetrahydro-pyran-3-carbonyl]-oxazolidin-2-one (177 mg, 0.453 mmol) in 4:1 tetrohydrofuran:water (2.27 mL) at 0° C. was added lithium hydroxide (17.3 mg, 0.724 mmol) dissolved in 900 μL of water. To the resulting solution was added 30 wt % aqueous hydrogen peroxide (205 μL) dropwise, and the now pale yellow solution was stirred for 30 min. The solution was then poured into water (50 mL) containing a 1.5 mL-aliquot of 1.3 M sodium sulfite, and the resulting aqeuous layer was acidified with 6N aqueous hydrogen chloride (10 mL). The aqueous layer was washed with ethyl acetate (3×50 mL), and the combined organic layers were washed with brine (15 mL), dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 33% ethyl acetate in hexanes) to yield the desired product 100 mg (95%) as a pale yellow oil. MS (ESI), m+/z: (M+H)+=233.2.

1. washThe aqueous layer was washed with ethyl acetate (3×50 mL)
2. washthe combined organic layers were washed with brine (15 mL)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe resulting residue was purified by flash chromatography (SiO2, 33% ethyl acetate in hexanes)

ORD record

ord-d6be355418c4421f95a990994b86d90e

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627629B2