Acetic Acid → HCID 12834012, compound

HRID 1660618Notes

Reaction equation

HRID 1660618 reaction equation
C(O)(=O)C.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14]CC(Cl)(Cl)Cl)=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])[C@H:8]2[S:7]1.Cl.C(OCC)(=O)C>CN(C)C=O.[Zn]>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])[C@H:8]2[S:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 128340092,2,2-Trichloroethyl 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylate

Product 1

HCID 12834012HCID 12834012, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Acetic acid (8 ml) and zinc powder (6 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylate (4.1 g) in anhydrous dimethylformamide (30 ml), and the mixture was stirred for 1 hour under ice-cooling and then 3.5 hours at room temperature. After the reaction, 10% hydrochloric acid and ethyl acetate were added to the reaction mixture. The insoluble material was filtered off and the ethyl acetate layer was separated, and then extracted with a sodium bicarbonate aqueous solution. The extract was acidified with 10% hydrochloric acid and extracted with ethyl acetate, after which the extract was dried over magnesium sulfate. After the solvent was distilled off, the residue was crystallized by adding ether to give 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylic acid (1.0 g), mp 148° to 151° C.

Workup

  1. stirringthe mixture was stirred for 1 hour under ice-
  2. temperaturecooling
  3. custom3.5 hours
  4. customat room temperature
  5. additionwere added to the reaction mixture
  6. filtrationThe insoluble material was filtered off
  7. customthe ethyl acetate layer was separated
  8. extractionextracted with a sodium bicarbonate aqueous solution
  9. extractionextracted with ethyl acetate
  10. dry with materialafter which the extract was dried over magnesium sulfate
  11. distillationAfter the solvent was distilled off
  12. customthe residue was crystallized
  13. additionby adding ether

Sources & evidence

ORD record
ord-126d3d694112413980e70528e2fdc20f
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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