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m-Chloroperbenzoic acid → (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130503
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 130503
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15]([C@:17]1([N:39]=[N+:40]=[N-:41])[C@H:22]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:21][C@@H:20]2[C@H:18]1[C@@:19]2([F:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:16])[CH3:13]>ClCCl>[CH2:12]([O:14][C:15]([C@:17]1([N:39]=[N+:40]=[N-:41])[C@H:22]([S:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)=[O:9])[CH2:21][C@@H:20]2[C@H:18]1[C@@:19]2([F:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:16])[CH3:13]
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Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86606014(1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Produkt 1

HCID 86606015(1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl esterAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

32 mg of 3-chloroperbenzoic acid was added to 73 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 1.46 mL of dichloromethane and the mixture was stirred for 1 hour in a dry ice-acetone bath. The mixture was stirred for 3.5 hours in an ice bath, and further stirred for 11 hours at room temperature. 15 mg of 3-chloroperbenzoic acid was further added thereto, and the mixture was stirred for 1 hour in a dry ice-acetone bath, and then stirred for 4 hours in an ice bath. The reaction solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=4:1 to 2:1), thereby yielding 63 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester and 12 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfonyl-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Aufarbeitung

  1. stirringThe mixture was stirred for 3.5 hours in an ice bath
  2. stirringfurther stirred for 11 hours at room temperature
  3. stirringthe mixture was stirred for 1 hour in a dry ice-acetone bath
  4. stirringstirred for 4 hours in an ice bath
  5. washThe reaction solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=4:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7007f06c0471475a98e70969cfd22741
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07381746B2

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