Norborna-diene → HCID 69363436, Verbindung

HRID 723755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723755
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]=[N+:27]=[N-:28])[O:22][C:21]3=[O:29])=[CH:16][C:15]=2[F:30])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31]12CC(CC1)=C[CH:32]=2>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]4[CH:32]=[CH:31][N:28]=[N:27]4)[O:22][C:21]3=[O:29])=[CH:16][C:15]=2[F:30])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 18006658Norborna-dieneHCID 86590232HCID 86590232, Verbindung

Produkt 1

HCID 69363436HCID 69363436, VerbindungAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(5R)-3-(4-((3R)-3-(t-Butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5-azidomethyl-oxazolidin-2-one (695 mg, 1.65 mM) was dissolved in dioxane (30 ml), treated with norbornadiene (760 mg, 8.25 mM) and heated under reflux for 6 hours. After removal of the solvent, the residue was dissolved in the minimum of dichloromethane and purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 2.5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (544 mg).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in the minimum of dichloromethane
  5. custompurified by chromatography on a 20 g silica Mega Bond Elut® column
  6. washeluting with a gradient
  7. temperatureincreasing in polarity from 0 to 2.5% methanol in dichloromethane
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0ebd0d0638c3456e8c36fbfbdceb29a2
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141583B2

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