Ethanol → Squalamine dilactate

HRID 1012909Notes

Reaction equation

HRID 1012909 reaction equation
[CH3:1][C@@H:2]([C@@H:14]1[C@@:18]2([CH3:43])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:41])[CH2:27][CH2:28][C@H:29]([NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:30][C@@H:25]4[CH2:24][C@@H:23]([OH:42])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:3][CH2:4][C@@H:5]([O:9][S:10]([OH:13])(=[O:12])=[O:11])[CH:6]([CH3:8])[CH3:7].[C:44]([OH:49])(=[O:48])[C@H:45]([CH3:47])[OH:46].C(O)C>>[CH3:1][C@@H:2]([C@@H:14]1[C@@:18]2([CH3:43])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:41])[CH2:27][CH2:28][C@H:29]([NH:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH2:30][C@@H:25]4[CH2:24][C@@H:23]([OH:42])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:3][CH2:4][C@@H:5]([O:9][S:10]([OH:13])(=[O:12])=[O:11])[CH:6]([CH3:7])[CH3:8].[CH3:47][C@H:45]([OH:46])[C:44]([OH:49])=[O:48].[CH3:47][C@H:45]([OH:46])[C:44]([OH:49])=[O:48]

Participants

4

Reactant 3

HCID 702EthanolHCID 72495SqualamineHCID 107689L-Lactic Acid

Product 1

HCID 11948287Squalamine dilactateYield 76%

Procedure

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.

Workup

  1. customRecrystallization
  2. customto form a cloudy solution
  3. filtrationThe solution was filtered through a filter
  4. filtrationwith filter aid
  5. washthe filter cake washed with 650 ml
  6. filtrationThe resulting solution was filtered through a 0.22 μm
  7. filtrationfilter
  8. filtrationthe container and filter
  9. washwashed with 650 ml
  10. temperatureThe filtrate was cooled to about 0 to about 5° C. for at least 12 hours
  11. stirringwithout stirring
  12. additionapproximately 100 mg of recrystallized squalamine dilactate seed crystals were added
  13. temperatureThe solution was maintained at about 0 to about 5° C.
  14. stirringwithout stirring for at least 48 more hours
  15. customthe resulting precipitation
  16. stirringwas agitated at less than about 5° C.
  17. customto form a homogeneous suspension
  18. customThe solids were collected
  19. washthe filter cake washed with 650 ml
  20. customof cold (0 to 5° C.) ethanol
  21. customThe product was dried in vacuo at about 40° C. (±2° C.)

Sources & evidence

ORD record
ord-86ffc79134704492af8c08dff26382e6
Source dataset
uspto-grants-2011_07
Patent number
US07981876B2

Reaction notes

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