DL-alanine → 2-(Cyclopentylformamido)propanoic acid

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.

1. customAt 0° C
2. waitat 40° C. for 1 h
3. temperatureThe solution is cooled to −10° C.
4. stirringThe mixture is stirred at −10° C. for 2 h and at room temperature for 1 h
5. temperatureWith ice-cooling
6. stirringthe mixture is stirred for 10 min.
7. filtrationthe resulting precipitate is filtered off with suction
8. washThe precipitate is washed with 300 ml of water
9. dry with materialwith 300 ml of diethyl ether and subsequently dried at 60° C.

ORD record

ord-d94f79942acd4abda53fdab727364607

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098207B2