Hydrogen Peroxide → (R)-tert-butoxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acid

To a solution of [(R)-2-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-1-(4-methoxy-3-methyl-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (6.05 g, 13.3 mmol) in 4:1 tetrahdydrofuran/water (200 mL) at −10° C. was added sequentially 30% aqueous hydrogen peroxide (15 mL, 133 mmol) and a solution of lithium hydroxide monohydrate (1.63 g, 40 mmol) in water (20 mL). The reaction mixture was stirred at −10° C., and the progress of the reaction was monitored by thin layer chromatography. After 4 hours, thin layer chromatography indicated almost complete consumption of starting material. Saturated aqueous sodium sulfite solution (100 mL) was added. The mixture was concentrated to half of its original volume under reduced pressure to remove tetrahydrofuran, then extracted with dichloromethane (2×100 mL). The aqueous layer was separated and acidified to pH=4 with aqueous citric acid solution, extracted with ethyl acetate (2×250 mL). The organic layers were separated, combined, dried over sodium sulfate, concentrated under reduced pressure and dried in vacuo to give (R)-tert-butoxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acid as a white foam (2.2 g, 58%).

1. customconsumption of starting material
2. additionSaturated aqueous sodium sulfite solution (100 mL) was added
3. concentrationThe mixture was concentrated to half of its original volume under reduced pressure
4. customto remove tetrahydrofuran
5. extractionextracted with dichloromethane (2×100 mL)
6. customThe aqueous layer was separated
7. extractionextracted with ethyl acetate (2×250 mL)
8. customThe organic layers were separated
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customdried in vacuo

ORD 기록

ord-95384d5044f74850a00dad2edf50ab0f

출처 데이터셋

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07427635B2