Реакция #2079

ord-1079585e7a194106a0429ed7ca89727f

Уравнение реакции

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate
→
C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-benzyloxycarbonyloxy-5-androsten-17-one

Реактанты

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate

Реагенты

Нет

Растворители

ClCCl
methylene chloride

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Промывкаthe mixture is washed with water
  2. 2
    Другоеevaporated to dryness
  3. 3
    workup.DISSOLUTIONThe residue is then dissolved in acetone
  4. 4
    Другоеprecipitated in iced water
  5. 5
    workup.WAITAfter 16 h
  6. 6
    Фильтрацияcrystals are filtered
  7. 7
    Другоеdried in vacuo

Методика

To a stirred solution of dehydroepiandrosterone (2.88 % 10 mmol) in methylene chloride (100 mL) is added dropwise benzylchloroformate, over a period of 30 min following the known procedure (F. Reber and T. Reichstein, Helv. Chim. Acta, 28, 1164, 1945). After stirring for 3 h, the mixture is washed with water and evaporated to dryness. The residue is then dissolved in acetone and precipitated in iced water. After 16 h, crystals are filtered and dried in vacuo.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05728688uspto-grants-1998_03