Sodium Azide → HCID 18594802, Verbindung

HRID 1580230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1580230
CS(O[CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O>[N:31]([CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)=[N+:32]=[N-:33]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 18594876HCID 18594876, Verbindung

Produkt 1

HCID 18594802HCID 18594802, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1.35 g. of ethyl 15-methanesulfonyloxy 9-oxo-prostanoate (Example 90) in 60 ml. of N,N-dimethylformamide containing 1.25 g. of sodium azide is heated on the steam-bath for 18 hours. The cooled solution is poured into 300 ml. of water and the resulting mixture is extracted several times with ether. The combined ether extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness. The residual oil is chromatographed on silica gel to give 737 mg. (62%) of oil; λmax. 4.77 (azido) and 5.78 μ (carbonyl groups).

Aufarbeitung

  1. additionThe cooled solution is poured into 300 ml
  2. extractionof water and the resulting mixture is extracted several times with ether
  3. washThe combined ether extracts are washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe residual oil is chromatographed on silica gel
  6. customto give 737 mg

Quellen und Nachweise

ORD-Eintrag
ord-db3368590273442d99e3a69612b4ba01
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03932472

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