Water → HCID 70503192, compound

HRID 1979791Notes

Reaction equation

HRID 1979791 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[C:15](=[O:23])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.C(=O)([O-])O.[Na+].O.O.[Cl-].[Ca+2].[Cl-].O>CO.C(OCC)(=O)C>[C:18]([NH:17][CH:16]1[C:15](=[O:23])[N:10]2[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][O:4][CH3:1])[CH2:7][S:8][C@H:9]12)(=[O:22])[CH:19]([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6093260Calcium chloride, dihydrateHCID 70503504HCID 70503504, compound

Product 1

HCID 70503192HCID 70503192, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2 g of 3-acetoxymethyl-7-isobutyrylamino-3-cephem-4-carboxylic acid and 490 mg of sodium hydrogen carbonate were dissolved in 21 ml of 66% v/v aqueous methanol, and 30 g of calcium chloride dihydrate were added. The resulting mixture was stirred at 70° C. for 90 minutes, after which it was cooled and 40 ml of water and 50 ml of ethyl acetate were added. The aqueous phase was adjusted to a pH value of 7-8 and separated, after which it was acidified with hydrochloric acid and extracted three times, each time with 50 ml of ethyl acetate. The extracts were combined, and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and concentrated by evaporation under reduced pressure. The residue was dissolved in a small volume of ethyl acetate, and insolubles were filtered off. Diisopropyl ether was added to the filtrate, and the resulting precipitates were collected by filtration and dried, giving 800 mg (yield 43.5%) of the title compound.

Workup

  1. additionwere added
  2. temperatureafter which it was cooled
  3. customseparated
  4. extractionextracted three times
  5. washthe combined extracts were washed with an aqueous solution of sodium chloride
  6. concentrationconcentrated by evaporation under reduced pressure
  7. dissolutionThe residue was dissolved in a small volume of ethyl acetate, and insolubles
  8. filtrationwere filtered off
  9. additionDiisopropyl ether was added to the filtrate
  10. customthe resulting precipitates
  11. filtrationwere collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-858edb0f7383430c8d3cbd33b4fd28c4
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

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