반응 #5643

반응 방정식

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

sodium hydride

4-bromobenzenesulfonyl chloride

→

title compound

수율 54.1%

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

수율 54.1%

용매

acetonitrile

hydrogen

반응 조건

후처리

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

실험 절차

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.

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