Malonic Acid → FTY720 Malonate

HRID 1191971Notes

Reaction equation

HRID 1191971 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([NH2:22])([CH2:20][OH:21])[CH2:18][OH:19])=[CH:13][CH:14]=1.[ClH:23].[C:24]([OH:30])(=[O:29])[CH2:25][C:26]([OH:28])=[O:27]>C(OCC)(=O)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:22])([CH2:18][OH:19])[CH2:20][OH:21])=[CH:11][CH:10]=1.[ClH:23].[C:24]([O-:30])(=[O:29])[CH2:25][C:26]([O-:28])=[O:27]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 107969Fingolimod Hydrochloride

Product 1

HCID 131731258FTY720 Malonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In an alternative procedure, FTY720 free base (2.27 mmol) was dissolved in ethyl acetate (16 ml) at 88 to 90° C. Then a solution of malonic acid (1.14 mmol) in ethyl acetate (3 ml) was added at 75° C., whereupon the product started to crystallize out immediately after addition. The resulting suspension was cooled to room temperature. The product was collected by filtration and was washed with ethyl acetate (2 ml). After drying at 50° C. the product (788 mg) was obtained as white crystals.

Workup

  1. customto crystallize out immediately
  2. additionafter addition
  3. filtrationThe product was collected by filtration
  4. washwas washed with ethyl acetate (2 ml)
  5. dry with materialAfter drying at 50° C. the product (788 mg)
  6. customwas obtained as white crystals

Sources & evidence

ORD record
ord-59ac6e63c08148389ff8239bf049c003
Source dataset
uspto-grants-2014_03
Patent number
US08680146B2

Reaction notes

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