반응 #2079

ord-1079585e7a194106a0429ed7ca89727f

반응 방정식

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

반응물

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

시약

없음

용매

ClCCl
methylene chloride

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척the mixture is washed with water
  2. 2
    기타evaporated to dryness
  3. 3
    workup.DISSOLUTIONThe residue is then dissolved in acetone
  4. 4
    기타precipitated in iced water
  5. 5
    workup.WAITAfter 16 h
  6. 6
    여과crystals are filtered
  7. 7
    기타dried in vacuo

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05728688uspto-grants-1998_03