Hydrochloric Acid → HCID 67439351, compound

Participants

Reaction Steps

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.65 g, 19.1 mmol) was added to a solution of the sodium salt of 5-(2,3-difluorophenyl)-6-[(2,4-dimethoxybenzyl)amino]hexanoic acid (8.58 g, 17.3 mmol) in acetonitrile (346 mL). After 2 h, hydrochloric acid (4.0 M in dioxane; 13.0 mL; 52.0 mmol) was added. After 16 h, additional N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.24 g, 16.9 mmol), 1-hydroxybenzotriazole hydrate (1.0 g, 6.53 mmol) and triethylamine (4.83 mL, 34.6 mmol) were added. After 16 h, the reaction mixture was concentrated. The mixture was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→96% dichloromethane/methanol) gave the title compound (4.72 g). MS 376.1 (M+1).

Provenance & Evidence