Reaktion #1067252

ord-ca7b4c4470604a14a7c67a4d63294e19

Reaktionsgleichung

CC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CC[C@H](F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β,24S]-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate
O=C([O-])O.[Na+]
sodium bicarbonate
CC1(C)C(=O)N(Br)C(=O)N1Br
1,3-dibromo-5,5-dimethylhydantoin
→
CC(=O)O[C@@H]1CC2=CC(Br)[C@H]3[C@@H]4CC[C@H]([C@H](C)CC[C@H](F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β,7ξ,24S]-7-bromo-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate

Edukte

CC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CC[C@H](F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β,24S]-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate
O=C([O-])O.[Na+]
sodium bicarbonate
CC1(C)C(=O)N(Br)C(=O)N1Br
1,3-dibromo-5,5-dimethylhydantoin

Reagenzien

Keine

Lösungsmittel

CCCCCC
hexane

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONA mixture of 0.260 g
  2. 2
    Temperaturcooled
  3. 3
    FiltrationThe mixture was filtered
  4. 4
    Sonstigethe solids were triturated with hexane
  5. 5
    Filtrationfiltered
  6. 6
    SonstigeThe combined filtrates were evaporated to dryness

Vorschrift

A mixture of 0.260 g. (0.0005 mole) of [1α,3β,24S]-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate, 0.25 g. of sodium bicarbonate, 0.096 g. (0.00033 mole) of 1,3-dibromo-5,5-dimethylhydantoin, and 13 ml. of hexane was heated at reflux (80° C.) for 1 hr and cooled. The mixture was filtered and the solids were triturated with hexane and filtered. The combined filtrates were evaporated to dryness to yield [1α,3β,7ξ,24S]-7-bromo-24-fluorocholest-5-en-1,3,25-triol 1,3-diacetate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04634692uspto-grants-1987_01