Sulfuric Acid → HCID 70456312, compound

HRID 482827Notes

Reaction equation

HRID 482827 reaction equation
[CH2:1]([CH:3]1[CH:6]([CH2:7][CH2:8][OH:9])[NH:5][C:4]1=[O:10])[CH3:2].[Mn]([O-])(=O)(=O)=[O:12].[K+].P([O-])(O)(O)=O.[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>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

7

Reactant 5

HCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 516951Monobasic potassium phosphateHCID 656671Sodium PyrosulfiteHCID 13619047HCID 13619047, compound

Product 1

HCID 70456312HCID 70456312, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

The crude 3-ethyl-4-[2-(hydroxy)ethyl]-2-azetidinone (34 g; 0.237 mol) obtained according to step (c) is added to 63 g (0.394 mol) of potassium permanganate and 79 g (0.59 mol) of potassium dihydrogen phosphate in 870 ml of water. The mixture is maintained under stirring at 15° C. for 22 hours, then 220 ml of a saturated solution of sodium metabisulfite are added thereto maintaining the value of the pH at about 3 by the gradual addition of 220 ml of 10% sulfuric acid. The mixture is stirred under cooling at 5° C. until a clear solution is obtained (about 30 minutes), then, after saturation with ammonium sulfate, it is extracted with four 250-ml portions of ethyl acetate. The organic extracts are pooled together and dried over MgSO4. Concentration of the ethyl acetate solution to 100 ml and cooling overnight in a refrigerator gives a crystalline precipitate which is recovered by filtration. Yield 16.43 g of the product of the title. Concentration of the mother liquors yields 2.23 g of the product. Elemental analysis, I.R. and N.M.R. data are in agreement with the assigned structure.

Workup

  1. temperatureThe mixture is maintained
  2. temperaturethereto maintaining the value of the pH at about 3
  3. stirringThe mixture is stirred
  4. temperatureunder cooling at 5° C. until a clear solution
  5. customis obtained (about 30 minutes)
  6. extractionafter saturation with ammonium sulfate, it is extracted with four 250-ml portions of ethyl acetate
  7. dry with materialdried over MgSO4
  8. temperatureConcentration of the ethyl acetate solution to 100 ml and cooling overnight in a refrigerator
  9. customgives a crystalline precipitate which
  10. filtrationis recovered by filtration

Sources & evidence

ORD record
ord-9f59222617074e70b0174cb36d0132a3
Source dataset
uspto-grants-1986_03
Patent number
US04576746

Reaction notes

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