Dimethyl Sulfide → Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

HRID 704264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704264
[CH:1]([NH:3][CH:4]1[C:28](=[O:29])[N:6]2[CH:7]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:8](=C)[CH2:9][S:10][C@H:5]12)=[O:2].[O:30]=[O+][O-].CSC>C(Cl)Cl.CO>[CH:1]([NH:3][CH:4]1[C:28](=[O:29])[N:6]2[C:7]([C:12]([O:14][CH:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:8]([OH:30])[CH2:9][S:10][C@H:5]12)=[O:2]

Komponenten

6

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 86744523Benzhydryl 7-formamido-3-methylenecepham-4-carboxylate

Produkt 1

HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of benzhydryl 7-formamido-3-methylenecepham-4-carboxylate (40.8 g) in methylene chloride (300 ml) and methanol (1.2 l) was cooled at -74° C. in a dry ice-acetone bath. A theoretical amount of ozone was blown through the solution at -74° C. for 10 minutes with stirring, and nitrogen gas was blown through the solution at -74° C. for 10 minutes Dimethyl sulfide (20 ml) was added to the solution at -74° C. The mixture was slowly warmed to ambient temperature and evaporated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate. The eluent was evaporated in vacuo to give benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (34.4 g).

Aufarbeitung

  1. customevaporated in vacuo
  2. washeluted with ethyl acetate
  3. customThe eluent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d2a2342ac7d4f258d81df17c3e3f13e
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985555

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