Reaction #1914845

ord-cdacb88d8c1b43aabac33e30350acad4

Reaction equation

O=C(Cl)CCCBr
4-bromobutanoylchloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone
→
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO.O=C([O-])CCCBr
Hydrocortisone 4-bromobutanoate

Reactants

O=C(Cl)CCCBr
4-bromobutanoylchloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Dryingdried over P2O5
  2. 2
    workup.ADDITIONThe solution was treated with water
  3. 3
    Otherthe organic phase was separated
  4. 4
    Dryingdried (Na2SO4)

Procedure

Five portions of 4-bromobutanoylchloride (0.35 ml×5) and potassium carbonate (0.4 g×5) were added in 24 hours to a solution of hydrocortisone (1 g) in CHCl, dried over P2O5 and stirred for 5 days. The solution was treated with water, the organic phase was separated, dried (Na2SO4) and deprived of the solvent at reduced pressure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07056905B2uspto-grants-2006_06