Реакция #48895

ord-4a21139022934614aaca272b8999f93e

Уравнение реакции

C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@]2(C)[C@@]1(O)C(=O)CO
1-3
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@]2(C)[C@@]1(O)C(=O)CO
(11β,16β)-9-fluoro-17,21-dihydroxy-16-methyl-3,20-dioxo-11-trifluoroacetoxy-pregna-1,4-diene
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)OCC(=O)[C@@]1(O)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@@]21C
1-4
Выход 94.7%
CC(=O)OCC(=O)[C@@]1(O)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@@]21C
(11β,16β)-9-fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-trifluoroacetoxy-21-acetoxy-pregna-1,4-diene
Выход 94.7%

Реактанты

C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@]2(C)[C@@]1(O)C(=O)CO
1-3
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](OC(=O)C(F)(F)F)C[C@]2(C)[C@@]1(O)C(=O)CO
(11β,16β)-9-fluoro-17,21-dihydroxy-16-methyl-3,20-dioxo-11-trifluoroacetoxy-pregna-1,4-diene
CC(=O)OC(C)=O
acetic anhydride

Реагенты

CN(C)c1ccncc1
DMAP

Растворители

C1CCOC1
THF

Условия реакции

Температура
35°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThe solvent was evaporated
  2. 2
    workup.ADDITIONthe residue diluted with 1 L of water
  3. 3
    ДругоеThe precipitate was isolated by filtration
  4. 4
    Другоеdried for 15 hrs in

Методика

To a solution of 1-3 (122.5 g) in THF (1 L) at RT was added DMAP (6.0 g, 49 mmol) and acetic anhydride (50.2 g, 491 mmol) and the mixture allowed to stir for 15 hours. The solvent was evaporated, and the residue diluted with 1 L of water. The precipitate was isolated by filtration and dried for 15 hrs in a warm (35° C.) vacuum oven to produce 123.4 g (94.7%) 1-4 as an off-white solid.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07745657B2uspto-grants-2010_06