Imino and amino sugar purification
View Patent ↗Novel processes for the purification of an imino or amino sugar, such as D-1-deoxygalactonojirimycin (DGJ). Particularly, there are described processes for the purification of multi-kilogram scale sugars using hydrochloric acid.
1. A method for the purification of a crude D-1-deoxygalactonojirimycin contaminated with an alkali- or alkali earth metal-containing compound comprising:
(a) admixing
D-1-deoxygalactonojirimycin with a solution having at least 35% hydrochloric acid or with hydrogen chloride gas to saturation to form a chloride salt of the alkali- or alkali earth metal-containing compound;
(b) forming the chloride salt of the alkali- or alkali earth metal-containing compound;
(c) removing the chloride salt of the alkali- or alkali earth metal-containing compound wherein the chloride salt is a solid; and
(d) crystallizing D-1-deoxygalactonojirimycin by addition of a solvent miscible with hydrochloric acid.
2. The method of claim 1 , wherein D-1-deoxygalactonojirimycin is mixed with water and then saturated with hydrogen chloride gas.
3. The method of claim 1 , wherein D-1-deoxygalactonojirimycin is mixed with a solution having at least 35% hydrochloric acid.
4. The method of claim 1 , wherein the alkali- or alkali earth metal-containing compound was formed from the addition of sodium methoxide.
5. The method of claim 1 , wherein crystallizing D-1-deoxygalactonojirimycin comprises adding a water/ethanol solvent mixture.
6. The method of claim 1 , wherein the amount of metal-containing compound is reduced to less than 0.01% by weight following step (d).
7. The method of claim 1 , wherein D-1-deoxygalactonojirimycin is at least 98% pure following step (d).
8. The method of claim 1 , wherein D-1-deoxygalactonojirimycin is at least 99% pure following step (d).
9. The method of claim 1 , wherein at least 5 kg of D-1-deoxygalactonojirimycin is produced following purification.
10. The method of claim 1 , further comprising synthesizing D-1-deoxygalactonojirimycin from a sugar starting material.
11. A method for purification of a crude D-1-deoxygalactonojirimycin or the HCl salt thereof contaminated with an alkali- or alkali earth metal-containing compound comprising:
(a) admixing the crude D-1-deoxygalactonojirimycin or the HCl salt thereof with a solution having at least 35% hydrochloric acid or with hydrochloric gas to saturation to form a chloride salt of the alkali- or alkali earth metal-containing compound;
(b) forming the chloride salt of the alkali- or alkali earth metal-containing compound;
(c) removing the chloride salt of the alkali- or alkali earth metal-containing compound; and
(d) crystallizing D-1-deoxygalactonojirimycin.HCl.
12. The method of claim 11 , wherein crystallizing D-1-deoxygalactonojirimycin.HCl comprises adding a water/ethanol solvent mixture.
13. The method of claim 11 , wherein D-1-deoxygalactonojirimycin.HCl is at least 98% pure following step (d).
14. The method of claim 11 , wherein D-1-deoxygalactonojirimycin.HCl is at least 99% pure following step (d).
15. The method of claim 11 , further comprising synthesizing D-1-deoxygalactonojirimycin.HCl from a sugar starting material.
16. The method of claim 15 , where the sugar starting material is a galactose.
17. The method of claim 1 , further comprising removing the chloride salt of the alkali- or alkali earth metal-containing compound by filtration.
18. The method of claim 11 , further comprising removing the chloride salt of the alkali- or alkali earth metal-containing compound by filtration.
19. The method of claim 1 , wherein the crude D-1-deoxygalactonojirimycin is a 5-amino-5-deoxy-D-galactopyranose derivative of the form:
20. The method of claim 11 , wherein the D-1-deoxygalactonojirimycin or the HCl salt thereof is admixed with a solution having at least 35% HCl.