تفاعل #215039

ord-70ce152f981c4a4daab53b5c389e1097

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةis refluxed for 3.0 hours
  2. 2
    أخرىThe isopropanol is then removed by distillation in vacuo
  3. 3
    غسيلthe residue is washed with water
  4. 4
    أخرىdried
  5. 5
    أخرىcrystallized

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04257969uspto-grants-1981_03