Tetrahydrofuran → methyl (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Participants

Reaction Steps

The mixture of 41.7 g (0.153 mol) methyl (R)-2-amino-3-(3,4-diethyl-phenyl)-propionate, 800 mL THF and 28 mL (0.161 mol) ethyldiisopropylamine was combined with 25.4 g (0.157 mol) CDT and then 38.0 g (0.155 mol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one while cooling with an ice bath and refluxed for 3 h with stirring. The reaction mixture was then extracted with 300 mL 10% citric acid solution, three times with 100 mL aliquots of water and 200 mL saturated NaCl solution, dried and evaporated down under reduced pressure.

Provenance & Evidence