Sodium Hydroxide → (4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one

HRID 604560Notes

Reaction equation

HRID 604560 reaction equation
C(OC([NH:8][C@:9]([CH3:28])([CH:19]=[CH:20][C:21]1[N:22]([CH2:26][CH3:27])[CH:23]=[CH:24][CH:25]=1)[CH2:10][O:11][C:12](=[O:18])CCCCC)=O)(C)(C)C.[OH-].[Na+].CC(C)([O-])C.[K+]>O1CCCC1.CO.C(O)(=O)C.C(OCC)(=O)C.O>[CH3:28][C@@:9]1([CH:19]=[CH:20][C:21]2[N:22]([CH2:26][CH3:27])[CH:23]=[CH:24][CH:25]=2)[CH2:10][O:11][C:12](=[O:18])[NH:8]1

Participants

9

Reactant 3

HCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxideHCID 66673020(2R)-2-t-Butoxycarbonylamino-2-methyl-4-(1-ethylpyrrol-2-yl)-1-n-hexanoyloxy-3-butene

Product 1

HCID 66673008(4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-oneYield 86.8%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

(2R)-2-t-Butoxycarbonylamino-2-methyl-4-(1-ethylpyrrol-2-yl)-1-n-hexanoyloxy-3-butene (11.7 g, 29.8 mmol) obtained in Reference example 3 (3b) was dissolved in a mixture of tetrahydrofuran (40 mL) and methanol (40 mL) and a 2N aqueous sodium hydroxide solution (40 mL) was added thereto, followed by stirring of the mixture at room temperature for 1 hour and 30 minutes. Acetic acid (1.5 mL) was added to the reaction mixture to stop the reaction and water and ethyl acetate were added thereto to separate it. The thus obtained organic phase was separated, washed with water and 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 (8.7 g). A solution of potassium t-butoxide (4.0 g, 35.6 mmol) in tetrahydrofuran (30 mL) was added to a solution of the crude product (8.7 g) in tetrahydrofuran (100 mL) under ice-cooling over 10 minutes, followed by stirring of the mixture at the same temperature for 1 hour. Acetic acid (2 mL) was added to the reaction mixture to neutralize it, and the mixture was concentrated under reduced pressure and water and ethyl acetate were added thereto to separate it. The thus obtained organic phase was 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, 3:2) to obtain the title compound (5.7 g, yield: 86%).

Workup

  1. additionwere added
  2. customto separate it
  3. customThe thus obtained organic phase was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customto obtain a crude product (8.7 g)
  9. temperaturecooling over 10 minutes
  10. stirringby stirring of the mixture at the same temperature for 1 hour
  11. concentrationthe mixture was concentrated under reduced pressure and water and ethyl acetate
  12. additionwere added
  13. customto separate it
  14. washThe thus obtained organic phase was washed 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, 3:2)

Sources & evidence

ORD record
ord-d8a7d9104f7f4c9f9fc6c443e8bd87e6
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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