Réaction #56294

Équation de réaction

7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid sodium salt

N-tosylphthalimide

triethylamine

→

7β-(2-thienylacetamido)-3-[2-(N-tosylcarbamoyl) benzoyloxy]methyl-3-cephem-4-carboxylic acid sodium salt

Rendement 58.5%

Solvants

N,N-dimethylformamide

water

Conditions de réaction

Traitement

1. 1
   Lavagerinsed with ethyl acetate
2. 2
   Extractionextracted with ethyl acetate
3. 3
   AutreThe extract is dried
4. 4
   workup.ADDITIONa solution of sodium 2-ethylhexanoate in isopropyl alcohol is added

Mode opératoire

In N,N-dimethylformamide (40 ml) is dissolved in 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid sodium salt (3.8 g), followed by the addition of N-tosylphthalimide (4.0 g) and triethylamine (2.0 ml) in that order. The mixture is stirred at room temperature for 4 hours. The reaction mixture is poured in water (100 ml) and rinsed with ethyl acetate. The aqueous layer is adjusted to pH 2.0 with dilute phosphoric acid and extracted with ethyl acetate. The extract is dried and, then, a solution of sodium 2-ethylhexanoate in isopropyl alcohol is added. By this procedure is obtained 7β-(2-thienylacetamido)-3-[2-(N-tosylcarbamoyl) benzoyloxy]methyl-3-cephem-4-carboxylic acid sodium salt (4.0 g).

Source