(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → Methyl 3-[5-(3-methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoate

HRID 14090

Reaktionsgleichung

Reaktionsgleichung von HRID 14090
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6](=[O:21])[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])=O.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[O:21][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[N:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 21086156Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

Produkt 1

HCID 21086154Methyl 3-[5-(3-methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate (520 mg, 1.7 mmol) is dissolved in anhydrous tetrahydrofuran (4 mL), and (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (810 mg, 3.4 mmol). The reaction is microwaved (100 W, 2 min) in a sealed vessel, cooled, filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica gel, 40% ethyl acetate/hexanes) gives the title compound. ESI MS m/z 290.1 [M+H]+.

Aufarbeitung

  1. customThe reaction is microwaved (100 W, 2 min) in a sealed vessel
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (silica gel, 40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c5d6bb3e939a42238c4088f41c35ccc8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

Verknüpfte Notizen

Wird geladen…