Carbon Tetrachloride → 4(S)-[1(S)-azido-2-phenylethyl]-1,3,2-dioxathiolane 2,2-dioxide

HRID 1080515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080515
[S:1](Cl)(Cl)=[O:2].[N:5]([C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:9]([OH:12])[CH2:10][OH:11])=[N+:6]=[N-:7].C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:26].[Na+]>O.O.O.[Ru](Cl)(Cl)Cl.O.C(OCC)C.C(#N)C>[N:5]([C@H:8]([C@H:9]1[CH2:10][O:11][S:1](=[O:2])(=[O:26])[O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N+:6]=[N-:7]

Komponenten

9

Edukt 4

HCID 5943Carbon TetrachlorideHCID 24386Thionyl ChlorideHCID 11117244(2S,3S)-3-azido-4-phenylbutane-1,2-diolHCID 23667635Sodium periodate

Produkt 1

HCID 104682854(S)-[1(S)-azido-2-phenylethyl]-1,3,2-dioxathiolane 2,2-dioxideAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 12090026Ruthenium chloride trihydrateKatalysatorHCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

175 μl (2.4 mmol) of thionyl chloride were added to a solution of 414 mg (2 mmol) of 3(S)-azido-4-phenyl-1,2(S)-butanediol [prepared as described in Example 2(vi)]in 5 ml of carbon tetrachloride and the mixture was heated under reflux for 30 minutes with calcium chloride drying tube protection. The resulting solution was cooled in an ice bath, 5 ml of acetonitrile, 5 mg of ruthenium-(III) chloride trihydrate, 642 mg (3 mmol) of sodium metaperiodate and 7.5 ml of water were added in succession and the mixture was stirred vigorously at room temperature for 1 hour. The mixture was treated with 20 ml of diethyl ether and 20 ml of water, the phases were separated and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined and washed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution. After drying over anhydrous magnesium sulphate, filtration through diatomaceous earth and evaporation of the filtrate there were obtained 518 mg of 4(S)-[1(S)-azido-2-phenylethyl]-1,3,2-dioxathiolane 2,2-dioxide; MS: m/e 270 [M+H]+.

Aufarbeitung

  1. customprepared
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 30 minutes with calcium chloride drying tube protection
  4. temperatureThe resulting solution was cooled in an ice bath
  5. customthe phases were separated
  6. extractionthe aqueous phase was extracted twice with diethyl ether
  7. washwashed with water, saturated aqueous sodium bicarbonate solution and sodium chloride solution
  8. dry with materialAfter drying over anhydrous magnesium sulphate, filtration through diatomaceous earth and evaporation of the filtrate there

Quellen und Nachweise

ORD-Eintrag
ord-bc5a496fefea4328b4481018842f5cde
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580999

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