Acetone → HCID 70504162, compound

HRID 1979793Notes

Reaction equation

HRID 1979793 reaction equation
C[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.C(=O)([O-])O.[Na+].[Cl-].[Ca+2].[Cl-].[O:27]([CH2:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:38][C:39](C)=O>CO.O>[CH:11]1([NH2+:8][CH:7]2[CH2:6][CH2:15][CH2:39][CH2:38][CH2:16]2)[CH2:10][CH2:9][CH2:33][CH2:28][CH2:29]1.[CH3:2][O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[CH:10]([NH:13][C:35](=[O:36])[CH2:34][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([O-:18])=[O:17]

Participants

8

Reactant 5

HCID 180Acetone2×HCID 69703Phenoxyacetyl chlorideHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 5284359Calcium Chloride

Product 1

HCID 70504162HCID 70504162, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5 g of 7-aminocephalosporanic acid and 3.1 g of sodium hydrogen carbonate were dissolved in 50 ml of 66% v/v aqueous methanol, and 75 g of anhydrous calcium chloride were added. The mixture was then stirred at 70° C. for 1.5 hours, after which it was cooled, 100 ml of water and 50 ml of acetone were added, and the mixture was ice-cooled. To the mixture was then added dropwise, with stirring, a solution of 3.75 g of phenoxyacetyl chloride in 20 ml of acetone and the mixture was allowed to stand at room temperature for 30 minutes. The mixture was then concentrated by evaporation under reduced pressure to about two thirds of its original volume, and then 200 ml of ethyl acetate and hydrochloric acid were added. The mixture was extracted twice, each time with 100 ml of ethyl acetate. The extracts were combined, washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure. The residue was dissolved in about 30 ml of ethyl acetate, and insolubles were filtered off. 3 g of dicyclohexylamine were added to the filtrate, and the mixture was left to stand for 30 minutes at room temperature and then for 3 hours with ice-cooling. The crystals which were produced were collected by filtration and dried, giving 2.1 g (yield 20.4%) of the title compound.

Workup

  1. additionwere added
  2. temperatureafter which it was cooled
  3. temperaturecooled
  4. additionTo the mixture was then added dropwise
  5. stirringwith stirring
  6. waitto stand at room temperature for 30 minutes
  7. concentrationThe mixture was then concentrated by evaporation under reduced pressure to about two thirds of its original volume
  8. addition200 ml of ethyl acetate and hydrochloric acid were added
  9. extractionThe mixture was extracted twice
  10. washwashed with an aqueous solution of sodium chloride
  11. concentrationconcentrated by evaporation under reduced pressure
  12. dissolutionThe residue was dissolved in about 30 ml of ethyl acetate
  13. filtrationinsolubles were filtered off
  14. addition3 g of dicyclohexylamine were added to the filtrate
  15. waitthe mixture was left
  16. waitto stand for 30 minutes at room temperature
  17. temperaturefor 3 hours with ice-cooling
  18. customThe crystals which were produced
  19. filtrationwere collected by filtration
  20. customdried

Sources & evidence

ORD record
ord-744024e427f14a5ba537aec0b28c441a
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

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