Réaction #4533

Équation de réaction

thionyl chloride

p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

2,6-dimethylpyridine

→

title compound

p-Nitrobenzyl 2-(4-Ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThis was followed by dropwise addition of a solution of 1.73 ml
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   AutreThe filtrate was evaporated to dryness in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 200 ml
5. 5
   LavageThe resulting solution was washed successively with dilute hydrochloric acid and water
6. 6
   Séchagedried with anhydrous sodium sulfate
7. 7
   AutreEvaporation in vacuo

Mode opératoire

To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran at 0°-5° C. was added 2.98 ml. of 2,6-dimethylpyridine. This was followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute period. Stirring was continued at 0°-5° C. for 15 minutes, and then the reaction mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was dissolved in 200 ml. of dichloromethane. The resulting solution was washed successively with dilute hydrochloric acid and water, and dried with anhydrous sodium sulfate. Evaporation in vacuo gave the title compound as a yellow, viscous liquid (yield: 7.12 g). The IR spectrum (CHCl3) of the product showed an absorption at 5.63 microns. The NMR spectrum (CDCl3) of the product showed absorptions at 1.3 (t, 3H); 2.47-3.7 (m, 4 H); 4.9-5.3 (m, 1H); 5.4 (s, 4H); 6.06 and 6.18 (ss, 1H); 7.58 (d, 2H); and 8.22 (d, 2H) ppm.

Source