반응 #92748

반응 방정식

sodium thiosulfate

sodium bicarbonate

8-(cyclohexylmethoxy)-N-[(1S)-1-(2-fluorophenyl)-3-hydroxypropyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one

→

(3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-3-(2-fluorophenyl)propanoic acid

수율 26.7%

용매

ethyl acetate

dichloromethane

반응 조건

후처리

1. 1
   기타a layer separation operation
2. 2
   세척The organic layer was washed with saturated aqueous sodium bicarbonate
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타the solvent was evaporated under reduced pressure
5. 5
   workup.ADDITIONTo a solution of the obtained residue and 230 μl of 2-methyl-2-butene in 6.5 ml of dioxane was added 1.7 ml of an aqueous solution of 93 mg of sodium chlorite and 315 mg of sodium dihydrogen phosphate in a water bath
6. 6
   workup.STIRRINGby stirring for 30 minutes in a water bath
7. 7
   workup.ADDITIONTo the reaction mixture were added water, 1 M hydrochloric acid, and chloroform
8. 8
   기타a layer separation operation
9. 9
   건조The organic layer was dried over anhydrous magnesium sulfate
10. 10
    기타the solvent was evaporated under reduced pressure
11. 11
    기타the obtained residue was purified by silica gel column chromatography
12. 12
    기타To the obtained purified product
13. 13
    workup.ADDITIONwas added diisopropyl ether
14. 14
    여과the resulting solid was filtered
15. 15
    기타dried

실험 절차

To a solution of 290 mg of 8-(cyclohexylmethoxy)-N-[(1S)-1-(2-fluorophenyl)-3-hydroxypropyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in dichloromethane was added 300 mg of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, followed by stirring overnight. To the reaction mixture were added saturated aqueous sodium bicarbonate, an aqueous sodium thiosulfate solution, and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a solution of the obtained residue and 230 μl of 2-methyl-2-butene in 6.5 ml of dioxane was added 1.7 ml of an aqueous solution of 93 mg of sodium chlorite and 315 mg of sodium dihydrogen phosphate in a water bath, followed by stirring for 30 minutes in a water bath. To the reaction mixture were added water, 1 M hydrochloric acid, and chloroform to carry out a layer separation operation. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. To the obtained purified product was added diisopropyl ether, and the resulting solid was filtered and dried to obtain 80 mg of (3S)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-3-(2-fluorophenyl)propanoic acid.

출처