Triethylamine → HCID 18462057, compound

Participants

Reaction Conditions

Reaction Steps

108.08 g (0.300 mol) of (+)-3-(3,4-dichlorophenyl)-3-benzyloxycarbonylpropionic acid and 154.11 g (0.300 mol) of 10-amino-1,2,3,4,6,7,8,9-octahydrobenzo[b][1,6]-naphthyridine were suspended in 600 ml of tetrahydrofuran, and the solution was cooled to an internal temperature of 20° C. Then 127.50 g (0.126 mol) of triethylamine was added at an internal temperature of 30° C. or below over a period of 15 minutes and the solution was further cooled to an internal temperature of 20° C., after which 210.00 g (0.330 mol) of a 50% ethyl acetate solution of T3P was added dropwise at an internal temperature of 25° C. over a period of 20 minutes and the solution was stirred at this temperature for 2 hours. The internal temperature of the solution was lowered to 20° C., then 1,200 ml of water was added dropwise at an internal temperature of 25° C. over a period of 10 minutes, and the precipitated crystals were centrifugally filtered by a centrifuge and washed twice with 360 ml of a 1/2 mixture of THF and water to obtain 271.48 g (100% yield) of the title compound.

Provenance & Evidence