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

HRID 130501
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 130501
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19]([C@:21]1([N:34]=[N+:35]=[N-:36])[C@@H:26](O)[CH2:25][C@@H:24]2[C@H:22]1[C@@:23]2([F:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:20])[CH3:17].N1C=CC=CC=1.C(OCC)C>ClCCl>[CH2:16]([O:18][C:19]([C@:21]1([N:34]=[N+:35]=[N-:36])[C@@H:26]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH2:25][C@@H:24]2[C@H:22]1[C@@:23]2([F:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:20])[CH3:17]
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 67749Trifluoromethanesulfonic anhydrideHCID 11185694(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Produkt 1

HCID 86606013(1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-77 °C

Versuchsvorschrift

0.36 mL of trifluoromethane sulfonic acid anhydride dissolved in 1.2 mL of dichloromethane was added dropwise to 364 mg of (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 6.1 mL of dichloromethane and 0.21 mL of pyridine at −77° C. to −69° C., under a nitrogen atmosphere. The mixture was stirred for 30 minutes at −77° C., and further stirred for 30 minutes at ice-cooling. 30 mL of diethyl ether was added thereto, and after the solids were filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1), thereby yielding 487 mg of (1R,2R,3S,5R,6R)-2-azido-6-fluoro-3-trifluoromethanesulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Aufarbeitung

  1. customat −77° C. to −69° C.
  2. stirringfurther stirred for 30 minutes at ice-
  3. temperaturecooling
  4. filtrationafter the solids were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel: Wako gel C200, eluent: hexane-ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-927355545dde4b4c8fd94e6ac22b8d76
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07381746B2

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