反应 #806279

反应方程式

diisopropylcarbodiimide

1-[bis(4-chlorophenyl)-methyl]azetidin-3-ylamine

toluenesulfonylacetic acid

hydroxybenzotriazole

→

N-{1-[bis(4-chlorophenyl)methyl]-azetidin-3-yl}-2-(toluene-4-sulfonyl)acetamide

溶剂

methanol

dichloromethane

dimethylformamide

dichloromethane

反应条件

后处理

1. 1
   workup.ADDITIONcontaining 1 g of SCX phase
2. 2
   洗涤After washing with twice 5 cm3 of methanol
3. 3
   洗涤4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol
4. 4
   workup.ADDITIONThe fraction containing the expected product
5. 5
   其他is evaporated under an air stream at a temperature in the region of 45° C.
6. 6
   其他dried under reduced pressure (1 mbar) at a temperature in the region of 40° C

实验过程

0.031 cm3 of diisopropylcarbodiimide, a solution of 30 mg of 1-[bis(4-chlorophenyl)-methyl]azetidin-3-ylamine in 0.5 cm3 of anhydrous dichloromethane, and 3 cm3 of anhydrous dichloromethane are added to a solution of 85.7 mg of toluenesulfonylacetic acid, 27 mg of hydroxybenzotriazole in solution in 0.5 cm3 of dimethylformamide under an inert argon atmosphere, at a temperature in the region of 23° C. After 17 hours at a temperature in the region of 23° C., the reaction mixture is loaded onto a 3-cm3 SPE cartridge containing 1 g of SCX phase preconditioned with methanol. After washing with twice 5 cm3 of methanol and then 4 cm3 of 0.1 N ammoniacal methanol, the expected product is eluted with 4 cm3 of 1 N ammoniacal methanol. The fraction containing the expected product is evaporated under an air stream at a temperature in the region of 45° C. and then dried under reduced pressure (1 mbar) at a temperature in the region of 40° C. N-{1-[bis(4-chlorophenyl)methyl]-azetidin-3-yl}-2-(toluene-4-sulfonyl)acetamide is obtained in the form of a yellow lacquer [1H NMR spectrum (500 MHz, CDCl3, δ in ppm): 2.85 (t, J=7 Hz: 2H); 3.07 (s: 3H); 3.48 (t, J=7 Hz: 2H); 4.24 (s: 1H); 4.49 (mt: 1H); 7.19 (broad d, J=6 Hz: 1H); from 7.20 to 7.40 (mt: 8H); 8.40 (s: 1H)].

来源