Dehydroepiandrosterone → 1476-64-8

HRID 617104Notes

Reaction equation

HRID 617104 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(Cl)Cl>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

6

Reactant 4

HCID 5881DehydroepiandrosteroneHCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 2723617Ethyl cysteinate hydrochloride2×

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 (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.

Workup

  1. temperaturethe mixture is heated overnight under an argon atmosphere
  2. filtrationThe solution is then filtered
  3. washthe filtrate is washed twice with water
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue is triturated with ethanol
  8. customto give crystals

Sources & evidence

ORD record
ord-cd606b7a281e4f33a5f3964028eaf489
Source dataset
uspto-grants-1999_09
Patent number
US05948434

Reaction notes

Loading…