Acetic Acid → (4R)-4-Methyl-4-[2-(1-methylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one

(2R)-2-t-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(1-methylpyrrol-2-yl)-3-butene (37.0 g, 97.8 mmol) obtained in Reference example 1 (1d) was dissolved in a mixture of tetrahydrofuran (100 mL) and methanol (100 mL) and a 2N aqueous sodium hydroxide solution (100 mL) was added thereto, followed by stirring of the mixture at room temperature for 1 hour. Water and methylene chloride were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain a crude product (28.8 g, yield: quantitative). A solution of potassium t-butoxide (13.2 g, 117 mmol) in tetrahydrofuran (80 mL) was added to a solution of the crude product in tetrahydrofuran (320 mL) under ice-cooling over 10 minutes and the mixture was stirred at the same temperature for 20 minutes. Acetic acid (6.7 mL, 117 mmol) was added to the reaction mixture to neutralize it and the mixture was concentrated under reduced pressure. Water and ethyl acetate were added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1-1:2) to obtain the title compound (20.3 g, yield: quantitative).

1. customto separate it
2. customThe thus obtained organic phase was separated
3. washwashed with a saturated aqueous NaCl solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. customthe solvent was evaporated under reduced pressure
7. customto obtain a crude product (28.8 g, yield: quantitative)
8. temperaturecooling over 10 minutes
9. stirringthe mixture was stirred at the same temperature for 20 minutes
10. concentrationthe mixture was concentrated under reduced pressure
11. additionWater and ethyl acetate were added
12. customto separate it
13. customThe thus obtained organic phase was separated
14. washwashed with a saturated aqueous NaCl solution
15. dry with materialdried over anhydrous sodium sulfate
16. filtrationAfter filtration
17. customthe solvent was evaporated under reduced pressure
18. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1-1:2)

ORD record

ord-8f64f2f48c3a4c28bacd98760aa9c04d

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910617B2