Sulfuric Acid → HCID 70456312, compound

HRID 482833Notes

Reaction equation

HRID 482833 reaction equation
[CH2:1]([CH:3]1[CH:6]([CH2:7][CH2:8][OH:9])[NH:5][C:4]1=[O:10])[CH3:2].P([O-])([O-])([O-])=[O:12].[Na+].[Na+].[Na+].OP([O-])(O)=O.[Na+].[OH-].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(=O)(O)O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O>[CH2:1]([C@@H:3]1[C:4](=[O:10])[NH:5][C@H:6]1[CH2:7][C:8]([OH:12])=[O:9])[CH3:2]

Participants

9

Reactant 7

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 516875Potassium Permanganate2×HCID 656671Sodium PyrosulfiteHCID 13619047HCID 13619047, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 70456312HCID 70456312, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the crude 3-ethyl-4-[2(hydroxy)ethyl]-2-azetidinone (6.41 g) obtained according to step (g) above, sodium phosphate bibasic (5.5 g) and sodium phosphate monobasic (3.4 g) in water (65 ml) is stirred for 20 minutes at room temperature. The pH of the solution is brought to 6.6 by the gradual addition of 10% sodium hydroxide (4.6 ml). The temperature is lowered to 15° C. and potassium permanganate (9.92 g) is added. The reaction mixture is stirred at 15°-20° C. for 24 hours maintaining the pH in the range of 6.6-8.5 by the gradual addition of 10% sulfuric acid (4.6 ml). The mixture is cooled to 5° C. and the excess of potassium permanganate is reduced by adding dropwise a 3.3M sodium meta-bisulfite solution (about 1.5 ml). After removing manganese dioxide by vacuum filtration on Celite, the clear aqueous solution is saturated with ammonium sulfate, brought to pH 3.5 with 10% sulfuric acid, and extracted with ethyl acetate (90 ml followed by four 40-ml portions). The combined extracts are dried over magnesium sulfate and concentrated under reduced pressure at 35° C. to a small volume. Crystallization is allowed to proceed at room temperature and then for two days at 0° C. The precipitate is removed by filtration and dried under vacuum. The yield in crystalline trans-(±)-3-ethyl-4-oxo-2-azetidinacetic acid is 3.2 g (48%).

Workup

  1. customobtained
  2. customis lowered to 15° C.
  3. stirringThe reaction mixture is stirred at 15°-20° C. for 24 hours
  4. temperaturemaintaining the pH in the range of 6.6-8.5
  5. temperatureThe mixture is cooled to 5° C.
  6. customAfter removing manganese dioxide
  7. filtrationby vacuum filtration on Celite
  8. extractionextracted with ethyl acetate (90 ml followed by four 40-ml portions)
  9. dry with materialThe combined extracts are dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure at 35° C. to a small volume
  11. customCrystallization
  12. customto proceed at room temperature
  13. waitfor two days at 0° C
  14. customThe precipitate is removed by filtration
  15. customdried under vacuum
  16. customThe yield in crystalline trans-(±)-3-ethyl-4-oxo-2-azetidinacetic acid

Sources & evidence

ORD record
ord-d1db24e19f7a4799b51ab6c9cfb3bbb1
Source dataset
uspto-grants-1986_03
Patent number
US04576746

Reaction notes

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