HCID 86720237, compound → HCID 86720236, compound

HRID 537725Notes

Reaction equation

HRID 537725 reaction equation
[C:1]([O:20][C@:21]1([C@:42]2([CH3:43])[C@H:28]([C@H:29]3[C:39](=[CH:40][CH2:41]2)[C@:37]2([CH3:38])[C:32](=[CH:33][C:34](=[O:44])[CH2:35][CH2:36]2)[CH2:31][CH2:30]3)[CH2:27][CH2:26]1)[C:22](=[O:25])[CH2:23][OH:24])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C(OC(=O)CCC)(=O)CCC.[Cl-].C([N+](CCCC)(CCCC)C)CCC>[C:1]([O:20][C@:21]1([C@:42]2([CH3:43])[C@H:28]([C@H:29]3[C:39](=[CH:40][CH2:41]2)[C@:37]2([CH3:38])[C:32](=[CH:33][C:34](=[O:44])[CH2:35][CH2:36]2)[CH2:31][CH2:30]3)[CH2:27][CH2:26]1)[C:22](=[O:25])[CH2:23][O:24][C:1](=[O:19])[CH2:2][CH2:3][CH3:4])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 86720237HCID 86720237, compound

Product 1

HCID 86720236HCID 86720236, compoundYield 159.2%

Reagents, catalysts & solvents 2

HCID 91822Tributylmethylammonium chlorideCatalystHCID 7798Butyric anhydrideSolvent

Procedure

the residue (6.2 g) of 17α-octadecanoyloxy-21-hydroxy-pregna-4,9(11)-diene-3,20-dione was dissolved in 4 ml butyric anhydride in the presence of 0.5 g of tributylmethylammonium chloride. The mixture was stirred at room temperature for 2 hours, then poured in ice and the resulting product was separated from water by extraction. The extract was washed to neutrality with water and concentrated under vacuum, the residue was crystallized from methanol to obtain 5.5 g (8.05 mM) of 17α-octadecanoyloxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione. This compound was used for the preparation of a pharmaceutical formulation in the form of a cream suitable for cutaneous administration.

Workup

  1. additionpoured in ice
  2. customthe resulting product was separated from water by extraction
  3. washThe extract was washed
  4. concentrationconcentrated under vacuum
  5. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-7afcf377e02c4bd9a4ac9e8586000322
Source dataset
uspto-grants-2014_10
Patent number
US08865690B2

Reaction notes

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