反応 #348496

反応方程式

water

p-nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide

N-chlorophthalimide

→

p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

溶媒

toluene

反応条件

後処理

1. 1
   温度Tolune (425 ml.) was heated in equipment
2. 2
   その他to azeotropically remove any moisture which
3. 3
   その他of toluene were removed
4. 4
   workup.ADDITIONTo the remaining toluene were added 10.0 g
5. 5
   温度below reflux
6. 6
   workup.DISTILLATIONToluene (200 ml.) was separately distilled
7. 7
   温度The resulting solution (warm)
8. 8
   workup.ADDITIONthroughout addition
9. 9
   温度The mixture then was refluxed for 55 minutes after which time a sample
10. 10
    その他was removed

実験手順

Tolune (425 ml.) was heated in equipment containing a Dean-Stark water trap to azeotropically remove any moisture which may be present, and 25 ml. of toluene were removed thereby. To the remaining toluene were added 10.0 g. (20 mmol.) of p-nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide, the toluene being maintained at a temperature slightly below reflux. Toluene (200 ml.) was separately distilled, and 4.0 g. (22 mmol.) of N-chlorophthalimide were added. The resulting solution (warm) was added dropwise to the solution of the penicillin sulfoxide ester over a period of 30 minutes. The mixture remained a light yellow solution throughout addition. The mixture then was refluxed for 55 minutes after which time a sample was removed, and nmr (CDCl3) analysis of the sample indicated virtually entire conversion of the penicillin sulfoxide ester to the title compound.

出典