Acetone → 16-Azido-3-methoxyestra-1(10),2,4-trien-17-one

HRID 1050287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050287
[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3].CC(C)=O.C(O)(C)C>S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C:5]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3]

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 3776IsopropanolHCID 21723401HCID 21723401, Verbindung

Produkt 1

HCID 16265816-Azido-3-methoxyestra-1(10),2,4-trien-17-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390chromium (VI) trioxideKatalysatorHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of 20 g 16α-azido-3-methoxy-estra-1,3,5(10)-triene-17β-ol in 11 acetone, 40 ml of 8 N chromium trioxide solution in conc. sulfuric acid is added dropwise at 0° C. and under stirring. After 2 h, 2 ml isopropanol are added and the reaction product is precipitated in crystalline form by dropwise addition of water. The product is filtered off, washed with water, dried and recrystallized from acetone/water. Yield: 16 g (81%), F=118-122° C.; [α]D+405°. IR: 1747 cm (CO), 2095 (N3).

Aufarbeitung

  1. customthe reaction product is precipitated in crystalline form by dropwise addition of water
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from acetone/water
  6. customYield: 16 g (81%), F=118-122° C.

Quellen und Nachweise

ORD-Eintrag
ord-47b6e540f34d4cbba60c0197cc9738c5
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382288B2

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