반응 #72551

반응 방정식

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

용매

CH3CN

THF

반응 조건

후처리

1. 1
   workup.ADDITIONthere is added
2. 2
   기타the temperature between −60° C. and −55° C
3. 3
   기타is brought to 0° C.
4. 4
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
5. 5
   기타the organic phases are evaporated in vacuo
6. 6
   추출the aqueous phase is extracted with DCM
7. 7
   기타The organic phase obtained
8. 8
   세척is washed with water
9. 9
   건조The organic phase is dried over sodium sulphate
10. 10
    여과filtered
11. 11
    기타evaporated to dryness
12. 12
    기타The product obtained
13. 13
    기타is recrystallised from a mixture of ethyl ether/ethanol
14. 14
    기타The crystals obtained
15. 15
    여과are filtered off
16. 16
    세척washed with ether
17. 17
    기타dried in vacuo at 40° C.

실험 절차

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.

출처