2,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate → 2,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate

HRID 647779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647779
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[C:15]([CH3:19])([CH2:17]Cl)[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N1C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:25])[Cl:26])=[O:21])=[C:15]([CH3:19])[CH2:17][S:16][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

3

Edukt 1

HCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Produkt 1

HCID 155734262,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylateAusbeute 25,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-chloromethylpenam-3-carboxylate (0.50 g.) in 1,1,2-trichloroethane(7 cc) and pyridine (0.16 g.) was heated under reflux for 3.5 hours. After cooling the reaction mixture was washed with water, dried and then concentrated under reduced pressure. The residue was subjected to chromatography on silica gel and eluated with chloroform. The eluate was concentrated and the residue was crystalized with ether to yield crystals (0.12 g.) of 2,2,2-trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 161°-162° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureAfter cooling the reaction mixture
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe eluate was concentrated
  8. customthe residue was crystalized with ether

Quellen und Nachweise

ORD-Eintrag
ord-7a8938c63f5c4ba2bb4d0f4959054ba2
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410458

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