반응 #87990

반응 방정식

sodium bicarbonate

3-amino-3-(pyridine-3-yl)propionic acid

trifluormethanesulfonyl chloride

→

pure product

수율 42.0%

4-(Pyridin-3-yl)azetidin-2-one

수율 42.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas slowly added
3. 3
   온도After cooling
4. 4
   workup.STIRRINGstirring in ice bath for 1 hour the reaction mixture
5. 5
   여과was filtered
6. 6
   세척washed three times with dry acetonitrile
7. 7
   기타the combined organic solutions were evaporated on a rotavapor at 35° C
8. 8
   추출The solid residue (23.8 g) was extracted in a Soxhlet-type extractor with boiling chloroform for 26 hours
9. 9
   기타The evaporation of the chloroform solution

실험 절차

To a mixture of 20.20 g (0.24 mole) sodium bicarbonate (Sigma, Ultrapure, dried in good vacuum at room temperature for 3 days over phosphorus pentoxide) and 6.64 g (0.04 mole) 3-amino-3-(pyridine-3-yl)propionic acid (Tyger, dried in good vacuum at room temperature for 3 days over phosphorus pentoxide) under argon atmosphere first 200 ml of dry acetonitrile (Fisher) was added then at very strong stirring 4.7 ml (0.044 mole) trifluormethanesulfonyl chloride (Acros) was slowly added and thereafter the reaction mixture was further stirred in an oil bath of 75-80° C. for 19 hours. After cooling and stirring in ice bath for 1 hour the reaction mixture was filtered, washed three times with dry acetonitrile and the combined organic solutions were evaporated on a rotavapor at 35° C. The solid residue (23.8 g) was extracted in a Soxhlet-type extractor with boiling chloroform for 26 hours. The evaporation of the chloroform solution gave 2.48 g (42%) pure product as white crystalline material (mp: 115-116° C.).

출처