反应 #5643

反应方程式

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

sodium hydride

4-bromobenzenesulfonyl chloride

→

title compound

收率 54.1%

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

收率 54.1%

溶剂

acetonitrile

hydrogen

反应条件

后处理

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

实验过程

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.

来源