Diisopropylethylamine → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-L-alanyl-L-alaninate

Participants

Reaction Steps

26.756 g (141.406 mmol) of N-(tert-butoxycarbonyl)-L-alanine together with 29.572 g (154.261 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 29.529 g (192.827 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 55.979 ml (321.378 mmol) of N,N-diisopropylethylamine were dissolved in 10 l DMF. 97.60 g (128.551 mmol) of trifluoroacetic acid-2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-alaninate (1:1) were then added, and the mixture was stirred at room temperature for 3 h. The reaction mixture was stirred into water and extracted with dichloromethane. The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated. The residue was triturated with diethyl ether, and the solid was filtered off with suction and air-dried. This gave 95 g (91% of theory) of the desired target compound.

Provenance & Evidence