反应详情

温度

90 °C

A 50% (by weight) solution of potassium carbonate (11.2 mL, 16.8 mmol, 1.02 eq), 8-aminocaprylic acid (9.5 g, 59.7 mmol, 1.00 eq), 5-fluoroisatoic anhydride (10.82 g, 59.7 mmol, 1.00 eq), dioxane (40 mL), and water (5 mL) were added to a 100 mL round bottom flask equipped with a magnetic stir bar and a condenser. The red cloudy mixture was heated to 90° C. for 2 hours (at which time the reaction was determined, by HPLC, to have finished). The deep purple solution was cooled to 25° C. and acidified to pH=4.0 with 3% (by vol.) aqueous hydrochloric acid. The dark precipitate which formed was isolated by filtration. The solid was recrystallized from 50 mL of 65% ethanol-water, recovered by filtration, and dried over 6 hours in a 50° C. vacuum oven. The N-(2-amino-5-fluorobenzoyl) -8-aminocaprylic acid was isolated as a light yellow solid (11.86 g, 67%), mp=108°-109° C.

1. customequipped with a magnetic stir bar and a condenser
2. temperatureThe deep purple solution was cooled to 25° C.
3. customThe dark precipitate which formed
4. customwas isolated by filtration
5. customThe solid was recrystallized from 50 mL of 65% ethanol-water
6. filtrationrecovered by filtration
7. customdried over 6 hours in a 50° C. vacuum oven