Ethanol → Squalamine dilactate

Participants

Reaction Steps

Recrystallization: Approximately 650 gms. (1.0 Mole) of crude squalamine was mixed into 11.05 L of ethanol to form a cloudy solution. The solution was filtered through a filter coated with filter aid and the filter cake washed with 650 ml. of ethanol. Approximately 494 ml of water and approximately 360.3 gms. (4.0 Moles) of L-(+) Lactic Acid was added to the filtered solution with stirring. The resulting solution was filtered through a 0.22 μm filter and the container and filter washed with 650 ml. of ethanol. The filtrate was cooled to about 0 to about 5° C. for at least 12 hours without stirring and then approximately 100 mg of recrystallized squalamine dilactate seed crystals were added. The solution was maintained at about 0 to about 5° C. without stirring for at least 48 more hours and then the resulting precipitation was agitated at less than about 5° C. to form a homogeneous suspension. The solids were collected and the filter cake washed with 650 ml. of cold (0 to 5° C.) ethanol. The product was dried in vacuo at about 40° C. (±2° C.) to yield a total of 614 g (76.0% yield) of crystallized squalamine dilactate. The synthesis scheme for crude squalamine dilactate is shown in FIG. 16.

Provenance & Evidence