Реакция #319375

Уравнение реакции

(4R)-4-benzyloxycarbonylamino-3-isoxazolidinone

Compound ( 1 )

1-(4-nitrobenzyl) 2-oxoglutarate

1-hydroxybenzotriazole

DCC

→

subject compound ( 8 )

Выход 75.7%

4-nitrobenzyl 2-[(4R)-4-benzyloxycarbonylamino-3-oxo-2-isoxazolidinyl]-5-oxo-2-tetrahydrofurancarboxylate

Выход 75.7%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеprepared by the method
2. 2
   workup.STIRRINGby stirring at room temperature for 30 minutes
3. 3
   ДругоеThe insolubles which separated out
4. 4
   Фильтрацияwere filtered off
5. 5
   Промывкаwashed with dichloromethane
6. 6
   Концентрированиеconcentrated
7. 7
   workup.DISSOLUTIONThe concentrate was dissolved in ethyl acetate
8. 8
   ПромывкаThe solution was washed with an aqueous solution of sodium hydrogen carbonate
9. 9
   Сушкаa saturated saline, successively, which was then dried (Na2SO4)
10. 10
    ДругоеThe solvent was evaporated off under reduced pressure
11. 11
    Промывкаfollowed by elution with hexane-ethyl acetate (1:1)

Методика

In 3 ml of dichloromethane were dissolved 85 mg of the Compound (1) obtained in Example 1 and 41 mg of 1-hydroxybenzotriazole (HOBT). To the solution was added 62 mg of DCC, and the mixture was stirred at room temperature for 30 minutes, to which was added 60 mg of (4R)-4-benzyloxycarbonylamino-3-isoxazolidinone, prepared by the method described in Journal of Medicinal Chemistry, 13 1013 (1970), followed by stirring at room temperature for 30 minutes. The insolubles which separated out were filtered off and washed with dichloromethane. The filtrate and the washing were combined and concentrated. The concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and a saturated saline, successively, which was then dried (Na2SO4). The solvent was evaporated off under reduced pressure, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 96 mg of the subject compound (8) as colorless foamy substance.

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