Dehydroepiandrosterone → 1476-64-8

HRID 2393260Notes

Reaction equation

HRID 2393260 reaction equation
[CH3:1][C@@:2]12[C:10](=O)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.C([O-])(=O)C.[Na+].Cl.C(OC(=O)[C@H](CS)N)C>C(O)C>[OH:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][CH2:10]2)[CH2:19]1

Participants

5

Reactant 3

HCID 5881DehydroepiandrosteroneHCID 517045Sodium AcetateHCID 2723617Ethyl cysteinate hydrochloride

Product 1

HCID 70566081476-64-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 evaporated 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.

Workup

  1. temperaturethe mixture is heated overnight under an argon atmosphere
  2. customThe reaction mixture is then evaporated under vacuum
  3. additionMethylene chloride is added to precipitate excess of L-cysteine ethyl ester hydrochloride
  4. filtrationThe solution is then filtered
  5. washthe filtrate is washed twice with water
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customThe residue is triturated with ethanol
  10. customto give crystals

Sources & evidence

ORD record
ord-997f98f87ab1467cae1898e36d3b3f61
Source dataset
uspto-grants-1998_09
Patent number
US05807849

Reaction notes

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