Reacción #56298

ord-5bcec5459bea4f9280758bd1ed364f42

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

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

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    SecadoThe ethyl acetate layer is dried
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    OtroThe residue is triturated with ether

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04224441uspto-grants-1980_09