Acetic Acid → FTY720 Acetate

HRID 1191972Notes

Reaction equation

HRID 1191972 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:27])(=[O:26])[CH3:25]>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-:27])(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 107969Fingolimod Hydrochloride

Product 1

HCID 131731259FTY720 Acetate

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 acetic acid (2.5 eq) 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 was obtained as white crystals in 99.4% 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 99.4% yield

Sources & evidence

ORD record
ord-403ad7c53915483ab76164cc34be85a4
Source dataset
uspto-grants-2014_03
Patent number
US08680146B2

Reaction notes

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