Реакция #215039

ord-70ce152f981c4a4daab53b5c389e1097

Уравнение реакции

COC(=O)C(=O)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
(11β,16α)-9-fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, methyl ester
[C-]#N.[Na+]
sodium cyanide
CC(C)O
isopropyl alcohol
→
CCCOC(=O)C(=O)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
title compound
CCCOC(=O)C(=O)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
(11β,16α)-9-Fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, 2-methylethyl ester

Реактанты

COC(=O)C(=O)[C@@]1(O)[C@H](O)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
(11β,16α)-9-fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, methyl ester
[C-]#N.[Na+]
sodium cyanide
CC(C)O
isopropyl alcohol

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураis refluxed for 3.0 hours
  2. 2
    ДругоеThe isopropanol is then removed by distillation in vacuo
  3. 3
    Промывкаthe residue is washed with water
  4. 4
    Другоеdried
  5. 5
    Другоеcrystallized

Методика

A solution of (11β,16α)-9-fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, methyl ester (1.0 g) in anhydrous isopropyl alcohol (100 ml) containing sodium cyanide (100 mg) is refluxed for 3.0 hours. The isopropanol is then removed by distillation in vacuo and the residue is washed with water, dried and crystallized to afford the title compound.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04257969uspto-grants-1981_03