Reacción #72551

Ecuación de reacción

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

Disolventes

CH3CN

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONthere is added
2. 2
   Otrothe temperature between −60° C. and −55° C
3. 3
   Otrois brought to 0° C.
4. 4
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
5. 5
   Otrothe organic phases are evaporated in vacuo
6. 6
   Extracciónthe aqueous phase is extracted with DCM
7. 7
   OtroThe organic phase obtained
8. 8
   Lavadois washed with water
9. 9
   SecadoThe organic phase is dried over sodium sulphate
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated to dryness
12. 12
    OtroThe product obtained
13. 13
    Otrois recrystallised from a mixture of ethyl ether/ethanol
14. 14
    OtroThe crystals obtained
15. 15
    Filtraciónare filtered off
16. 16
    Lavadowashed with ether
17. 17
    Otrodried in vacuo at 40° C.

Procedimiento

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.

Fuente