반응 #348428

반응 방정식

2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

sodium azide

acetone

→

2,2,2-trichloroethyl 2-azidomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

수율 14.9%

용매

water

반응 조건

후처리

1. 1
   기타After removing acetone under reduced pressure
2. 2
   추출the residue was extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer was washed with water, with a saturated sodium bicarbonate aqueous solution and further with water
4. 4
   건조dried over sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   workup.ADDITIONa small amount of ether was added to the residue
7. 7
   기타Precipitated crystals
8. 8
   여과were filtered off
9. 9
   workup.DISTILLATIONthe solvent was distilled off from the filtrate
10. 10
    기타The crystalline residue was purified by column chromatography on silica gel

실험 절차

A mixture of 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.08 g), sodium azide (0.26 g), acetone (20 ml) and water (4 ml) was stirred for 4 hours at room temperature. After removing acetone under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water, with a saturated sodium bicarbonate aqueous solution and further with water and then dried over sulfate. The solvent was distilled off under reduced pressure and a small amount of ether was added to the residue. Precipitated crystals were filtered off and the solvent was distilled off from the filtrate. The crystalline residue was purified by column chromatography on silica gel using chloroform as developing solvent to give 2,2,2-trichloroethyl 2-azidomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (150 mg). This substance was crystallized by adding a small amount of a mixture of ether and petroleum ether and the crystals were recrystallized from ether to give pure compound, mp 105° to 106° C.

출처