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Acetic Acid → 2-Methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid

HRID 1660614
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660614
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:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C@H:8]2[S:7]1>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:31])[CH:21]([NH:22][C:23](=[O:30])[CH2:24][C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)[C@H:8]2[S:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 12833985HCID 12833985, Verbindung

Produkt 1

HCID 128339882-Methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acidAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Acetic acid (3 ml) and zinc powder (2.4 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylate (1.8 g) in anhydrous dimethylformamide (10 ml), and the mixture was stirred for 1 hour at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was extracted by pouring into a mixture of 5% hydrochloric acid (50 ml) and ethyl acetate (40 ml). The ethyl acetate layer was washed with water and dried. After the solvent was distilled off, the residue was dissolved in ether and allowed to stand, after which the precipitating crystals were collected by filtration and dried to give 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid (1.2 g), mp 175° C. (dec.).

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. filtrationwas filtered off
  3. extractionthe filtrate was extracted
  4. additionby pouring into a mixture of 5% hydrochloric acid (50 ml) and ethyl acetate (40 ml)
  5. washThe ethyl acetate layer was washed with water
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. dissolutionthe residue was dissolved in ether
  9. filtrationafter which the precipitating crystals were collected by filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-489dde361e1f48b7b70f6f264e95b28d
Quelldatensatz
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04308380

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