34522-32-2 → HCID 3310216, compound

20 g of D-octopine in 100 ml of 1M NaOH was heated at 100° C. for 12-20 hr. The solution was evaporated to dryness to remove the ammonia and then dissolved in water. The pH was adjusted to 0.89 with 6M HCl and the solution was applied to a column of 200 g of Dowex-50 (H+ -form). The column was washed with water and then developed with 10% (v/v) aqueous ammonium hydroxide. The fractions that contained ninhydrin-positive material after removal of ammonia were combined, evaporated to dryness on a rotary evaporator, and then dissolved in 100 ml of water. The pH was adjusted to 5.2 with 3M HCl. After the addition of 5 volumes of ethanol, the solution was left at 0°-5° C. for 24 to 48 hr. A white solid was collected by filtration in an amount of 11.1 g, and identified as octopinic acid (67% yield, 99% pure). The absence of significant racemization at the chiral carbon atoms is supported by the fact that the product gave a single peak by HPLC in the 80% methanol in water, partisil SAX column solvent system that separates D-octopinic acid from L-allooctopinic acid and by its optical rotation ((α)D22 =20°, C 0.5, H2O; publ. 19°).

1. customThe solution was evaporated to dryness
2. customto remove the ammonia
3. dissolutiondissolved in water
4. washThe column was washed with water
5. customafter removal of ammonia
6. customevaporated to dryness on a rotary evaporator
7. dissolutiondissolved in 100 ml of water
8. additionAfter the addition of 5 volumes of ethanol
9. filtrationA white solid was collected by filtration in an amount of 11.1 g

ORD record

ord-949cbd42b3574046aaea8aa56aa23481

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04615976