Reaction #1914844

ord-81b7f41bd552435aa8af498604c46520

Reaction equation

O=C(Cl)CCCCl
4-chlorobutanoylchloride
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-])CCCCl
Hydrocortisone (4-chloro)butanoate
Yield 53.0%

Reactants

O=C(Cl)CCCCl
4-chlorobutanoylchloride
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

Solvents

CCN(CC)CC
triethylamine

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)
  5. 5
    Otherto give a white solid with a 53% yield by weight, which
  6. 6
    Othera melting point (m.p.) of 155° C.

Procedure

4 portions of 4-chlorobutanoylchloride (0.32 ml×4) and triethylamine (0.3 g×4) were added in 24 hours to a solution of hydrocortisone (1 g) in CHCl, dried over P2O5 and stirred for 3 days. The solution was treated with water, the organic phase was separated, dried (Na2SO4) and deprived of the solvent at reduced pressure. The crude residue was ground with hexane and CH2Cl2 to give a white solid with a 53% yield by weight, which had a melting point (m.p.) of 155° C.

Source

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