Diketene → HCID 88715150, compound

HRID 1979796Notes

Reaction equation

HRID 1979796 reaction equation
[CH3:1][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:3].[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1>[OH-].[Na+].C(OCC)(=O)C>[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[CH:10]([NH:13][C:22](=[O:23])[CH2:21][C:20](=[O:24])[CH3:19])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 88715150HCID 88715150, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

5.44 g of 7-aminocephalosporanic acid were dissolved in 20 ml of a 1N aqueous solution of sodium hydroxide, and 1.68 g of diketene were added, with ice-cooling, to the resulting solution. The mixture was stirred at the same temperature for 1 hour, after which it was diluted with 20 ml of ethyl acetate and then acidified. The mixture was extracted twice with ethyl acetate and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure, giving 4.4 g of the title compound as crystals melting at 150° C. (with decomposition).

Workup

  1. additionwere added, with ice-
  2. temperaturecooling, to the resulting solution
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washthe combined extracts were washed with an aqueous solution of sodium chloride
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-65c8e675f64c4b7191e5380d3f65b0ad
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

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