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Water → (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130500
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 130500
N([O-])=O.[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:23]([O:25][C:26]([C@:28]1([N:48]=[N+:49]=[N-:50])[C@H:33]([O:34]S(C(F)(F)F)(=O)=O)[CH2:32][C@@H:31]2[C@H:29]1[C@@:30]2([F:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:27])[CH3:24].O>CN(C)C=O>[CH2:23]([O:25][C:26]([C@:28]1([N:48]=[N+:49]=[N-:50])[C@@H:33]([OH:34])[CH2:32][C@@H:31]2[C@H:29]1[C@@:30]2([F:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:27])[CH3:24]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 2855718-Crown-6HCID 516910Potassium nitriteHCID 11154739(1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Produkt 1

HCID 11185694(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester
Ausbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

688 mg of potassium nitrite and 428 mg of 18-crown 6-ether was added to 701 mg of (1R,2R,3R,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 6.9 mL of N,N-dimethylformamide, and the mixture was stirred for 1.5 days at room temperature and further stirred for 3.5 days at 45° C., under a nitrogen atmosphere. Water was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1), thereby yielding 388 mg of (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2,6-diethyl ester.

Aufarbeitung

  1. stirringfurther stirred for 3.5 days at 45° C., under a nitrogen atmosphere
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e604ca975f643a3913b3b6f1a620bf8
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07381746B2

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