Process for preparing β-amino-α-hydroxycarboxamides
The present invention is directed to a process for preparing β-amino-α-hydroxycarboxamides. The process works with epoxycarboxamides of the formula 2 which are reacted with ammonia or other amines.
1. A salt comprising:
a) a compound of formula V:
in which R is a linear (C i -C 8 )-alkyl radical; and
b) a chiral acid wherein said chiral acid is an N-acylamino acid;
and wherein the 2S,3S isomer or the 2R,3R isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 90%.
2. The salt of claim 1 , wherein said compound of formula (V) is N-cyclopropyl-3-amino-2-hydroxyhexanamide.
3. The salt of claim 1 , wherein said N-acylamino acid is benzyloxycarbonyl-L-phenylalanine.
4. The salt of claim 3 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 95%.
5. The salt of claim 3 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 97%.
6. The salt of claim 1 , wherein said N-acylamino acid is acetyl-L-phenylalanine.
7. The salt of claim 6 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 95%.
8. The salt of claim 6 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 97%.
9. The salt of claim 2 , wherein said N-acylamino acid is acetyl-L-phenylalanine.
10. The salt of claim 9 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 95%.
11. The salt of claim 1 , wherein the 2R,3R isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 92%.
12. The salt of claim 1 , wherein the 2R,3R isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 95%.
13. The salt of claim 1 , wherein the 2R,3R isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 97%.
14. The salt of claim 1 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 92%.
15. The salt of claim 1 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 95%.
16. The salt of claim 1 , wherein the 2S,3S isomer of said compound of formula (V) is enantiomerically enriched in said salt by more than 97%.
17. The salt of claim 1 , comprising more than 90% 2S,3S-N-cyclopropyl-3-amino-2-hydroxyhexanamideN-benzyloxycarbonyl-L-phenylalanine.
18. The salt of claim 1 , comprising more than 92% 2S,3S-N-cyclopropyl-3-amino-2-hydroxyhexanamideN-benzyloxycarbonyl-L-phenylalanine.
19. The salt of claim 1 , comprising more than 95% 2S,3S-N-cyclopropyl-3-amino-2-hydroxyhexanamideN-benzyloxycarbonyl-L-phenylalanine.
20. The salt of claim 1 , comprising more than 97% 2S,3S-N-cyclopropyl-3-amino-2-hydroxyhexanamideN-benzyloxycarbonyl-L-phenylalanine.