Dichloromethane → Ammonium Hydroxide

Participants

Reaction Steps

N4-[2-(3-tert-Butoxycarbonylaminopropoxy)-4-methoxybenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (1.0 g, 1.8 mmol) was dissolved in ice cold dichloromethane (20 mL). Trifluoroacetic acid (10 mL) was then added and the mixture stirred on ice for 1 hour. Modest gas evolution was observed. The mixture was concentrated in vacuo. The oily residue was redissolved in 1:1 toluene:dichloromethane (20 mL) and reconcentrated to give a brown oil. The brown oil was vigorously stirred overnight with a mixture of dichloromethane (50 mL) and potassium carbonate (3.4 g) in water (50 mL). The organic layer was washed with brine, dried and concentrated to give partially pure N4-[2-(3-aminopropoxy)-4-methoxybenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine as a brittle brown foam (0.74 g, 90%, about 50%-60% pure via TLC (9:1 dichloromethane:MeOH w/few drops of ammonium hydroxide). This material was used without further purification.

Provenance & Evidence