تفاعل #48895

ord-4a21139022934614aaca272b8999f93e

معادلة التفاعل

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
المردود 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
المردود 94.7%

المتفاعلات

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

الكواشف

CN(C)c1ccncc1
DMAP

المذيبات

C1CCOC1
THF

ظروف التفاعل

درجة الحرارة
35°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07745657B2uspto-grants-2010_06