Dexamethasone → Deltasol

HRID 926810

Reaction equation

HRID 926810 reaction equation
[CH3:1][C@H:2]1[C@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[C@:18]2([CH3:25])[C@H:4]([C@H:5]3[C@:15]([F:27])([C@@H:16]([OH:26])[CH2:17]2)[C@:14]2([CH3:28])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1.[C:29]1(=[O:35])[O:34][C:32](=[O:33])[CH2:31][CH2:30]1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][C@H:2]1[C@:19]([OH:24])([C:20]([CH2:22][O:23][C:29]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:35])=[O:21])[C@:18]2([CH3:25])[C@H:4]([C@H:5]3[C@:15]([F:27])([C@@H:16]([OH:26])[CH2:17]2)[C@:14]2([CH3:28])[C:8](=[CH:9][C:10]([CH:12]=[CH:13]2)=[O:11])[CH2:7][CH2:6]3)[CH2:3]1

Participants

5

Reactant 2

HCID 5743DexamethasoneHCID 7922Succinic anhydride

Product 1

HCID 235849Deltasol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

An amount equivalent to 0.030 g of dexamethasone (1, 0.076 mmol, 1.0 equiv.) was completely dissolved in 1 mL of pyridine (non-anhydrous) and 0.038 g of succinic anhydride (0.382 mmol, 5.0 equiv.) was added to the clear solution. Then 1-2 mg of DMAP (7.6 μmol, 0.1 equiv.) was added to the solution and reaction was allowed to run for 48 h at r.t. under N2-flow. After 48 h, pyridine was evaporated under reduced pressure (in a rotary evaporator). A volume equivalent to 10 mL of H2O was added to the evaporated residue. A white precipitate was observed which was stirred for 10 minutes and then centrifuged. The resulting precipitate was washed again with 10 mL of H2O and the washed residue was lyophilized to yield the target product (2).

Workup

  1. waitAfter 48 h
  2. custompyridine was evaporated under reduced pressure (
  3. customin a rotary evaporator)
  4. additionA volume equivalent to 10 mL of H2O was added to the evaporated residue
  5. washThe resulting precipitate was washed again with 10 mL of H2O

Sources & evidence

ORD record
ord-2a33efbe14884b429230be4adb88a565
Source dataset
uspto-grants-2016_03
Patent number
US09289506B2

Linked notes

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