Acetic Acid → HCID 88734350, compound

HRID 1764034Notes

Reaction equation

HRID 1764034 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[N:5]2[C:16](=[O:31])[CH:17]([NH:18][C:19](=[O:30])[CH:20]([O:27][CH:28]=[O:29])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:4]2[S:3]1.C(O)(=O)C>[Zn].CN(C)C=O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:16](=[O:31])[CH:17]([NH:18][C:19](=[O:30])[CH:20]([O:27][CH:28]=[O:29])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C@H:4]2[S:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12834140HCID 12834140, compound

Product 1

HCID 88734350HCID 88734350, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trichloroethyl 2-methyl-7-(2-formyloxy-2-phenylacetamido)-3-cephem-4-carboxylate (1.58 g), zinc powder (1.5 g) and glacial acetic acid (1.5 ml) were added to anhydrous dimethylformamide (15 ml), and the mixture was stirred for 1 hour under ice-cooling. After the reaction, zinc powder was filtered off, and the filtrate was poured into a mixture of 5% hydrochloric acid (30 ml) and ethyl acetate (30 ml) and then extracted. The aqueous layer was further extracted twice with ethyl acetate (30 ml). The ethyl acetate layer was combined, and the combined solution was washed with 5% hydrochloric acid and water, and then dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was pulverized by adding isopropyl ether, followed by filtration, and dried to give amorphous 2-methyl-7-(2-formyloxy-2-phenylacetamido)-3-cephem-4-carboxylic acid (1.0 g).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into a mixture of 5% hydrochloric acid (30 ml) and ethyl acetate (30 ml)
  4. extractionextracted
  5. extractionThe aqueous layer was further extracted twice with ethyl acetate (30 ml)
  6. washthe combined solution was washed with 5% hydrochloric acid and water
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. additionby adding isopropyl ether
  10. filtrationfollowed by filtration
  11. customdried

Sources & evidence

ORD record
ord-5b3c4acdc8764feb9266393e9f0a3473
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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