Réaction #5643

Équation de réaction

diphenylmethyl 7-phenoxyacetamido-3 -hydroxy-3-cephem- 4-carboxylate

sodium hydride

4-bromobenzenesulfonyl chloride

→

title compound

Rendement 54.1%

Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

Rendement 54.1%

Solvants

acetonitrile

hydrogen

Conditions de réaction

Traitement

1. 1
   AutreThe title compound was prepared via a modification of the synthesis
2. 2
   AutreThe cooling bath was removed
3. 3
   workup.ADDITIONthe reaction mix
4. 4
   workup.STIRRINGstirred at room temperature for 19 hours
5. 5
   FiltrationThe reaction mixture was filtered
6. 6
   workup.ADDITIONthe filtrate carbon treated
7. 7
   AutreThe carbon was removed
8. 8
   Autreto leave a foam residue
9. 9
   AutreThe residue was crystallized from 1-propanol

Mode opératoire

The title compound was prepared via a modification of the synthesis described in U.S. Pat. No. 3,985,737. A solution of 0.51 g (0.001 mole) of diphenylmethyl 7-phenoxyacetamido-3 -hydroxy-3-cephem- 4-carboxylate in 5 mL of acetonitrile was cooled to 0° C. under a nitrogen atmosphere. Then 0.030 g (0.001 mole) of sodium hydride (80% in mineral oil) was added resulting in hydrogen evolution. The reaction mixture was stirred at 0° C. for 5 minutes, and 0.229 g (0.009 mole) of 4-bromobenzenesulfonyl chloride was added. The cooling bath was removed, and the reaction mix stirred at room temperature for 19 hours. The reaction mixture was filtered and the filtrate carbon treated. The carbon was removed followed by the solvent to leave a foam residue. The residue was crystallized from 1-propanol to yield 0.398 g (54%) of the title compound.

Source