Reaktion #449951

ord-51daf70e892b4cfe8172537080ef5107

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe mixture is heated overnight under an argon atmosphere
  2. 2
    FiltrationThe solution is then filtered
  3. 3
    Waschenthe filtrate is washed twice with water
  4. 4
    Sonstigedried on magnesium sulfate
  5. 5
    Filtrationfiltered
  6. 6
    Sonstigeevaporated under vacuum
  7. 7
    SonstigeThe residue is triturated with ethanol
  8. 8
    Sonstigeto give crystals

Vorschrift

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 (18g, 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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05872114uspto-grants-1999_02