Carbon Dioxide → Fingolimod phosphate

HRID 2053459Notes

Reaction equation

HRID 2053459 reaction equation
C1C2C(COC(=O)[NH:17][C:18]([CH2:41][O:42][P:43]([O:52]C3C=CC=CC=3)([O:45]C3C=CC=CC=3)=[O:44])([CH2:39][OH:40])[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=O)[CH2:28][CH2:29][CH2:30][CH2:31][C:32]4C=CC=[CH:34][CH:33]=4)=[CH:23][CH:22]=3)C3C(=CC=CC=3)C=2C=CC=1.C(=O)=O>>[NH2:17][C:18]([CH2:39][OH:40])([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:25][CH:26]=1)[CH2:41][O:42][P:43](=[O:44])([OH:45])[OH:52]

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 69200444HCID 69200444, compound

Product 1

HCID 9908268Fingolimod phosphate

Procedure

Compound obtained in step b) (0.32 g, 0.4 mmol) is dissolved in ethanovwater (10 ml, 3/2) and, after addition of barium hydroxyde-octahydrate (0,56 mg, 1.8 mmol), is kept at 75° C. for 14 hours. After cooling to RT the slurry is neutralized with solid carbon dioxide and filtered. The residue is dissolved in acetic acid (95%; 5 ml) and then diluted with water to a volume of 50 ml. The resulting precipitate is filtered off and dried over P4O10.

Workup

  1. filtrationfiltered
  2. dissolutionThe residue is dissolved in acetic acid (95%; 5 ml)
  3. additiondiluted with water to a volume of 50 ml
  4. filtrationThe resulting precipitate is filtered off
  5. dry with materialdried over P4O10

Sources & evidence

ORD record
ord-1b28219181bc4af1bd10000c5bfbf149
Source dataset
uspto-grants-2008_02
Patent number
US07326801B2

Reaction notes

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