Реакция #319389

Уравнение реакции

sodium hydride

(4R)-4-phenylacetamido-3-isoxazolidinone

Compound ( 28 )

benzyl 2-chloro-2,5-dihydro-5-oxo-2-furancarboxylate

→

subject Compound ( 32 )

Выход 20.1%

benzyl 2-[(4R)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

Выход 20.1%

Растворители

ethyl acetate

water

ethyl acetate

N,N-dimethylformamide

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.ADDITIONTo the solution was added, under ice-
2. 2
   Температураcooling
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGThe reaction solution was stirred at the same temperature for 45 minutes
5. 5
   Промывкаwashed with water
6. 6
   Сушкаdried (Na2SO4)
7. 7
   ДругоеThe solvent was evaporated off
8. 8
   Промывкаfollowed by elution with hexane-ethyl acetate (2:1)

Методика

In 3 ml of anhydrous N,N-dimethylformamide was dissolved 220 mg of (4R)-4-phenylacetamido-3-isoxazolidinone. To the solution was added, under ice-cooling and stirring, 60 mg of sodium hydride (50% mineral oil), which was stirred for 10 minutes. Then the reaction solution was cooled to -10° C., to which was added under stirring 0.7 ml of anhydrous N,N-dimethylformamide solution dissolving 250 mg of the Compound (28) obtained in Example 28. The reaction solution was stirred at the same temperature for 45 minutes, followed by pouring into a mixture of ethyl acetate and water. The ethyl acetate layer was taken, washed with water and dried (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1) to give 87 mg of the subject Compound (32) as colorless foamy substance.

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