反応 #87990

反応方程式

sodium bicarbonate

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

trifluormethanesulfonyl chloride

→

pure product

収率 42.0%

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

収率 42.0%

溶媒

acetonitrile

反応条件

後処理

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

実験手順

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.).

出典