2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate → 2-Methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylic acid

HRID 851616Notes

Reaction equation

HRID 851616 reaction equation
[CH3:1][C:2]1[S:3][C@@H:4]2[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16](=[O:28])[N:5]2[CH:6]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[CH:7]=1>CN(C)C=O.C(O)(=O)C.[Zn]>[CH3:1][C:2]1[S:3][C@@H:4]2[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:16](=[O:28])[N:5]2[CH:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

5

Reactant 1

HCID 131803442,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate

Product 1

HCID 128341842-Methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylic acidYield 62.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Zinc powder (1.8 g) was added under ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate (1.0 g) in a mixture of dimethylformamide (7.5 ml) and acetic acid (2.5 ml), and the mixture was stirred for 1.5 hours, followed by filtration of the reaction mixture, and the filtered zinc was washed with dimethylformamide (2 ml). The filtrate and the washings were combined and the combined solution was poured into a mixture of ethyl acetate (30 ml), ice-water (30 ml) and 10% hydrochloric acid (2 ml), after which the ethyl acetate layer was separated. The aqueous layer was further extracted with ethyl acetate (10 ml). The ethyl acetate layer was combined, and the combined solution was in turn washed with water, a saturated sodium chloride aqueous solution, dried over magnesium sulfate, after which the solvent was distilled off. The residue was crystallized by adding a small quantity of ether, after which the precipitated crystals were collected by filtration and dried to give colorless crystals of 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylic acid (0.45 g), mp 204° C.

Workup

  1. filtrationfollowed by filtration of the reaction mixture
  2. washthe filtered zinc was washed with dimethylformamide (2 ml)
  3. additionthe combined solution was poured into a mixture of ethyl acetate (30 ml), ice-water (30 ml) and 10% hydrochloric acid (2 ml)
  4. customafter which the ethyl acetate layer was separated
  5. extractionThe aqueous layer was further extracted with ethyl acetate (10 ml)
  6. washwashed with water
  7. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  8. distillationafter which the solvent was distilled off
  9. customThe residue was crystallized
  10. additionby adding a small quantity of ether
  11. filtrationafter which the precipitated crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-15b4ba4f3ab84ce29a63d41ee4a44cb0
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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