反応 #806278

反応方程式

diisopropylcarbodiimide

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

benzenesulfonylacetic acid

hydroxybenzotriazole

→

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

溶媒

methanol

dichloromethane

dimethylformamide

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONcontaining 1 g of SCX phase
2. 2
   洗浄After washing with twice 5 cm3 of methanol
3. 3
   洗浄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
   その他is evaporated under an air stream at a temperature in the region of 45° C.
6. 6
   その他dried under reduced pressure (1 mbar) at a temperature in the region of 40° C

実験手順

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 80.1 mg of benzenesulfonylacetic 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. 2-Benzenesulfonyl-N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}acetamide is thus obtained in the form of a white solid [1H NMR spectrum (500 MHz, CDCl3, δ in ppm): 2.96 (mt: 2H); 3.51 (mt: 2H); 4.00 (s: 2H); 4.34 (unresolved complex: 1H); 4.48 (mt: 1H); 7.10 (unresolved complex: 1H); from 7.20 to 7.45 (mt: 8H); 7.57 (t, J=8 Hz: 2H); 7.70 (t, J=8 Hz: 1H); 7.90 (d, J=8 Hz: 2H)].

出典