Reacción #4533

Ecuación de reacción

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

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente