Reaktion #348896

ord-5740e1a781c043a4b382872039c827dd

Reaktionsgleichung

O=P(O)(O)O
phosphoric acid
CCOC(=O)NS(=O)(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
[N-]=[N+]=[N-].[Na+]
sodium azide
O=C([O-])O.[Na+]
sodium bicarbonate
→
[N-]=[N+]=NCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid

Edukte

O=P(O)(O)O
phosphoric acid
CCOC(=O)NS(=O)(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid
[N-]=[N+]=[N-].[Na+]
sodium azide
O=C([O-])O.[Na+]
sodium bicarbonate

Reagenzien

Keine

Lösungsmittel

O=P([O-])([O-])[O-]
phosphate

Reaktionsbedingungen

Temperatur
60°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling
  2. 2
    Extraktionextracted with ethyl acetate
  3. 3
    TrocknenThe ethyl acetate layer is dried
  4. 4
    Einengenconcentrated under reduced pressure
  5. 5
    SonstigeThe residue is triturated with ether

Vorschrift

7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid-etherate (619 mg), sodium azide (100 mg) and sodium bicarbonate (84 mg) are dissolved in phosphate buffer solution (pH 6.4) (10 ml) and the mixture is stirred at 60° C. for one hour. After cooling, the reaction mixture is acidified by phosphoric acid and extracted with ethyl acetate. The ethyl acetate layer is dried and concentrated under reduced pressure. The residue is triturated with ether. The procedure provides 7β-(thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04166178uspto-grants-1979_08