Reacción #4530

Ecuación de reacción

p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate

m-chloroperbenzoic acid

→

p-Nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water
2. 2
   Secadodried over anhydrous sodium sulfate
3. 3
   Concentraciónconcentrated in vacuo to an oil
4. 4
   OtroThe crude title compound (1.25 g) was used without further purification
5. 5
   Otroabsorption bands at 5.6 and 5.79 microns

Procedimiento

A solution of 1.4 g p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 75 ml. methylene chloride was cooled to 0° C. under a nitrogen atmosphere. A solution of 0.551 g m-chloroperbenzoic acid in 25 ml methylene chloride was added dropwise, then the reaction mixture was stirred at 0° C. for 1 hour. The methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. The crude title compound (1.25 g) was used without further purification. The NMR spectrum of a deuterochloroform solution showed peaks at 1.24(m, 6H); 2.27-3.74(c, 13H); 4.7-5.46 (c, 3H); 7.57(m, 2H); and 8.23(m, 2H) ppm. The infrared spectrum of a dichloromethane solution has absorption bands at 5.6 and 5.79 microns.

Fuente