Acetic Acid → HCID 12833982, Verbindung

HRID 1660616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660616
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:33])[CH:21]([NH:22][C:23](=[O:32])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=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:33])[CH:21]([NH:22][C:23](=[O:32])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[C@H:8]2[S:7]1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 12833979HCID 12833979, Verbindung

Produkt 1

HCID 12833982HCID 12833982, VerbindungAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Acetic acid (4.1 ml) and zinc powder (3.4 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(3-chlorophenyl)acetamido]-3-cephem-4-carboxylate (2.6 g) in anhydrous dimethylformamide (30 ml), and the mixture was stirred for 1.5 hours at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was poured into a mixture of 5% hydrochloric acid (150 ml) and ethyl acetate (75 ml), and then extracted. The extract was washed with water and dried. After the solvent was distilled off, the residue was crystallized by adding acetonitrile. The crystals were collected by filtration, washed with ether and dried to give colorless crystals of 2-methyl-7-[2-(3-chlorophenyl)acetamido]-3-cephem-4-carboxylic acid (1.4 g), mp 173° to 174° C. (dec.).

Aufarbeitung

  1. stirringthe mixture was stirred for 1.5 hours at the same temperature
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into a mixture of 5% hydrochloric acid (150 ml) and ethyl acetate (75 ml)
  4. extractionextracted
  5. washThe extract was washed with water
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. customthe residue was crystallized
  9. additionby adding acetonitrile
  10. filtrationThe crystals were collected by filtration
  11. washwashed with ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2c52cd0ae6b644db90cc57cb16341f67
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04308380

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