Реакция #319395

Уравнение реакции

Compound ( 50 )

diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-3-phenylthio-2-tetrahydrofurancarboxylate

3-chloroperbenzoic acid

→

subject Compound ( 51 )

Выход 42.5%

diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

Выход 42.5%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ПромывкаThe reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water
2. 2
   Сушкаby drying (Na2SO4)
3. 3
   ДругоеThe solvent was then evaporated off
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 1 ml of toluene
5. 5
   ТемператураThe solution was heated at 80° C. for 30 minutes
6. 6
   Другоеthe solvent was evaporated off
7. 7
   Промывкаfollowed by elution with hexane-ethyl acetate (1:1)

Методика

In 3 ml of dichloromethane was dissolved 60 mg of the Compound (50) obtained in Example 50. To the solution was added 20 mg of 3-chloroperbenzoic acid. The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water, successively, followed by drying (Na2SO4). The solvent was then evaporated off, and the residue was dissolved in 1 ml of toluene. The solution was heated at 80° C. for 30 minutes, then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 21 mg of the subject Compound (51) as colorless crystals. The IR and NMR spectra of this product were in agreement with those of the compound obtained in (a) above.

Источник