반응 #215039

ord-70ce152f981c4a4daab53b5c389e1097

반응 방정식

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

반응물

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

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도is refluxed for 3.0 hours
  2. 2
    기타The isopropanol is then removed by distillation in vacuo
  3. 3
    세척the residue is washed with water
  4. 4
    기타dried
  5. 5
    기타crystallized

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04257969uspto-grants-1981_03