Propionic Acid → FTY720 Propionate

HRID 1191973Notes

Reaction equation

HRID 1191973 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:28])(=[O:27])[CH2:25][CH3:26]>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-:28])(=[O:27])[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 107969Fingolimod Hydrochloride

Product 1

HCID 131731260FTY720 Propionate

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 88-90° C. Then a solution of propionic acid (2.5 eq) in ethyl acetate (3 ml) was added at 70° 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 was obtained as white crystals in 96.9% yield.

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. customAfter drying at 50° C. the product
  6. customwas obtained as white crystals in 96.9% yield

Sources & evidence

ORD record
ord-be98c8ced2924515836b865271dc10c4
Source dataset
uspto-grants-2014_03
Patent number
US08680146B2

Reaction notes

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