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

HRID 1660627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660627
[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

Komponenten

5

Edukt 1

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

Produkt 1

HCID 128341842-Methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylic acidAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4d65dce35d864acca3ed8a7161631e51
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04308380

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