Thionyl Chloride → HCID 23152326, compound

Participants

Reaction Steps

To a solution of 2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionic acid (0.60 g, 1.26 mmol) in chloroform (18.0 ml) was added a catalytic amount of N,N-dimethylformamide, and thionyl chloride (0.28 ml, 3.78 mmol) was added dropwise under ice-cooling. The mixture was stirred for 2 hr. Then, the reaction mixture was evaporated under reduced pressure to give a yellow solid. Further, the obtained solid was dissolved in chloroform (2.5 ml) and added dropwise to a solution of methyl 3,4-diaminobenzoate (0.29 g, 1.76 mmol) in pyridine (1.5 ml) under ice-cooling. After dropwise addition, the mixture was warmed to room temperature, and the mixture was stirred at overnight. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution, methanol and water. The precipitate was collected by filtration, washed with water, and dried in vacuo to give methyl 4-amino-3-{2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionylamino}benzoate (0.73 g, yield 93%).

Provenance & Evidence