Реакция #72551

Уравнение реакции

triethylamine

HCl

ethyl(methylsulphanyl)-acetate

compound

3-(4-Amino-benzyl)-oxazolidin-2-one

tBuOCl

→

title product

3-Methylsulphanyl-5-(2-oxo-oxazolidin-3-ylmethyl)-1,3-dihydro-indol-2-one

Растворители

CH3CN

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONthere is added
2. 2
   Другоеthe temperature between −60° C. and −55° C
3. 3
   Другоеis brought to 0° C.
4. 4
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
5. 5
   Другоеthe organic phases are evaporated in vacuo
6. 6
   Экстракцияthe aqueous phase is extracted with DCM
7. 7
   ДругоеThe organic phase obtained
8. 8
   Промывкаis washed with water
9. 9
   СушкаThe organic phase is dried over sodium sulphate
10. 10
    Фильтрацияfiltered
11. 11
    Другоеevaporated to dryness
12. 12
    ДругоеThe product obtained
13. 13
    Другоеis recrystallised from a mixture of ethyl ether/ethanol
14. 14
    ДругоеThe crystals obtained
15. 15
    Фильтрацияare filtered off
16. 16
    Промывкаwashed with ether
17. 17
    Другоеdried in vacuo at 40° C.

Методика

To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl(methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step.

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