Reacción #5159

Ecuación de reacción

5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide

sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

dimethylformamide

→

title compound

Rendimiento 45.7%

5-Methyl-2-oxo-1,3-dioxolen-4-ylmethyl (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Rendimiento 45.7%

Disolventes

chloroform

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat 30°-45° C. for 4.5 hours
2. 2
   Lavadowashed four times with an aqueous solution of sodium chloride
3. 3
   OtroThe extract was dried
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   OtroThe residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A),
6. 6
   Lavadoeluted with a 10:1 by volume mixture of ethyl acetate and methanol

Procedimiento

A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 0.4 ml of dry dimethylformamide. The mixture was stirred at room temperature for 80 minutes and then at 30°-45° C. for 4.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed four times with an aqueous solution of sodium chloride. The extract was dried and the solvent was distilled off under reduced pressure. The residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A), eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 27.4 mg of the title compound in the form of a colorless powder.

Fuente