Reacción #704286

ord-cd606b7a281e4f33a5f3964028eaf489

Ecuación de reacción

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
CC(=O)[O-].[Na+]
sodium acetate
ClCCl
Methylene chloride
CCOC(=O)[C@@H](N)CS.Cl
L-cysteine ethyl ester hydrochloride
CCOC(=O)[C@@H](N)CS.Cl
L-cysteine ethyl ester hydrochloride
→
C[C@@]12CCC[C@H]1[C@@H]1CC=C3C[C@@H](O)CC[C@]3(C)[C@H]1CC2
3β-hydroxy-5-androstene

Reactantes

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
CC(=O)[O-].[Na+]
sodium acetate
ClCCl
Methylene chloride
CCOC(=O)[C@@H](N)CS.Cl
L-cysteine ethyl ester hydrochloride
CCOC(=O)[C@@H](N)CS.Cl
L-cysteine ethyl ester hydrochloride

Reactivos

Ninguno

Disolventes

CCO
ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe mixture is heated overnight under an argon atmosphere
  2. 2
    FiltraciónThe solution is then filtered
  3. 3
    Lavadothe filtrate is washed twice with water
  4. 4
    Otrodried on magnesium sulfate
  5. 5
    Filtraciónfiltered
  6. 6
    Otroevaporated under vacuum
  7. 7
    OtroThe residue is triturated with ethanol
  8. 8
    Otroto give crystals

Procedimiento

Following the procedure described by Djerassi (C. Djerassi, N. Crossley and M. A. Kielczewski, J. Org. Chem. 27, 1112, 1962), dehydroepiandrosterone (2.88 g, 10 mmol) is dissolved in anhydrous ethanol, sodium acetate is added followed by L-cysteine ethyl ester hydrochloride (18 g, 100 mmol) and the mixture is heated overnight under an argon atmosphere. The reaction mixture is then evaported under vacuum. Methylene chloride is added to precipitate excess of L-cysteine ethyl ester hydrochloride . The solution is then filtered and the filtrate is washed twice with water, dried on magnesium sulfate, filtered and evaporated under vacuum. The residue is triturated with ethanol to give crystals.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05948434uspto-grants-1999_09