Reaktion #448832

ord-39b45cba77a84200b7fde1648b31d129

Reaktionsgleichung

CCOC(C)=O
ethyl acetate
FC(F)(F)C(F)(F)CCC(CCCCl)SC(CCCCl)CCC(F)(F)C(F)(F)F
3-chloro-propyl-4,4,5,5,5-pentafluoropentylsulfide
CNCCCCC[C@@H]1Cc2cc(OC3CCCCO3)ccc2[C@H]2CC[C@]3(C)[C@@H](OC(C)=O)CC[C@H]3[C@H]12
17β-acetoxy-7α-(5-methylaminopentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene
[H-].[Na+]
sodium hydride
→
c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(COC3CCCCO3)CCC[C@@H]12
tetrahydropyran-2-yloxy-estra-1,3,5(10)-triene

Edukte

CCOC(C)=O
ethyl acetate
FC(F)(F)C(F)(F)CCC(CCCCl)SC(CCCCl)CCC(F)(F)C(F)(F)F
3-chloro-propyl-4,4,5,5,5-pentafluoropentylsulfide
CNCCCCC[C@@H]1Cc2cc(OC3CCCCO3)ccc2[C@H]2CC[C@]3(C)[C@@H](OC(C)=O)CC[C@H]3[C@H]12
17β-acetoxy-7α-(5-methylaminopentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene
[H-].[Na+]
sodium hydride

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

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

Aufarbeitung

  1. 1
    Waschenwashed with water
  2. 2
    Sonstigedried
  3. 3
    Einengenconcentrated by evaporation
  4. 4
    Sonstigethe residue is chromatographed on silica gel

Vorschrift

A solution of 1.64 g of 17β-acetoxy-7α-(5-methylaminopentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene in 25 ml of absolute DMF is stirred with 159 mg of 80% sodium hydride under nitrogen for 2 hours at room temperature. 1.43 g of 3-chloro-propyl-4,4,5,5,5-pentafluoropentylsulfide in 7 ml of absolute DMF is then added in drops and then stirred for 22 more hours at 80° C. The reaction solution is then diluted with ethyl acetate, washed with water, dried, concentrated by evaporation, and the residue is chromatographed on silica gel. 820 mg of 17β-acetoxy-7α-{5-[N-methyl-N-3-(4,4,5,5,5-pentafluoropentylthio)-propylamino]-pentyl}-3-(tetrahydropyran-2-yloxy-estra-1,3,5(10)-triene is obtained as oil. [α]D22 =+21.5°(c=0.51% in chloroform)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05866560uspto-grants-1999_02