Réaction #11354

Équation de réaction

cyclopentanecarbonyl chloride

D,L-alanine

triethylamine

trimethylsilyl chloride

→

2-Cyclopentanoylaminopropionic Acid

Solvants

dichloromethane

water

Conditions de réaction

Traitement

1. 1
   AutreAt 0° C
2. 2
   workup.WAITat 40° C. for 1 h
3. 3
   TempératureThe solution is cooled to −10° C.
4. 4
   workup.STIRRINGThe mixture is stirred at −10° C. for 2 h and at room temperature for 1 h
5. 5
   TempératureWith ice-cooling
6. 6
   workup.STIRRINGthe mixture is stirred for 10 min.
7. 7
   Filtrationthe resulting precipitate is filtered off with suction
8. 8
   LavageThe precipitate is washed with 300 ml of water
9. 9
   Séchagewith 300 ml of diethyl ether and subsequently dried at 60° C.

Mode opératoire

16.8 g (0.189 mol) of D,L-alanine and 41.98 g (0.415 mol) of triethylamine are initially charged in 200 ml of dichloromethane. At 0° C. 45.07 g (0.415 mol) of trimethylsilyl chloride are added dropwise, and the mixture is stirred at room temperature for 1 h and then at 40° C. for 1 h. The solution is cooled to −10° C., and 25 g (0.189 mol) of cyclopentanecarbonyl chloride are added dropwise. The mixture is stirred at −10° C. for 2 h and at room temperature for 1 h. With ice-cooling, 100 ml of water are added dropwise, the mixture is stirred for 10 min. and the resulting precipitate is filtered off with suction. The precipitate is washed with 300 ml of water and then with 300 ml of diethyl ether and subsequently dried at 60° C.

Source