Reacción #1914844

ord-81b7f41bd552435aa8af498604c46520

Ecuación de reacción

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
Rendimiento 53.0%

Reactantes

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

Reactivos

Ninguno

Disolventes

CCN(CC)CC
triethylamine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Secadodried over P2O5
  2. 2
    workup.ADDITIONThe solution was treated with water
  3. 3
    Otrothe organic phase was separated
  4. 4
    Secadodried (Na2SO4)
  5. 5
    Otroto give a white solid with a 53% yield by weight, which
  6. 6
    Otroa melting point (m.p.) of 155° C.

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07056905B2uspto-grants-2006_06