Dimethylformamide → HCID 178431719, Verbindung

HRID 2047475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047475
[CH3:1][C:2]([O:9][C:10](OC1C=CC([N+]([O-])=O)=CC=1)=[O:11])([CH3:8])[C:3](OCC)=[O:4].Cl.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][C:2]1([CH3:8])[O:9][C:10](=[O:11])[N:23]([C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:31])[CH2:26][CH2:25]2)[C:3]1=[O:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67232782Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoateHCID 178479264HCID 178479264, Verbindung

Produkt 1

HCID 178431719HCID 178431719, VerbindungAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the compound (1.3 g) obtained in step 1, benzyl trans-4-aminocyclohexanecarboxylate monohydrochloride (1.1 g), potassium carbonate (0.88 g) and DMF (30 mL) was stirred at 60° C. for 6 hr. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane) to give benzyl trans-4-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)cyclohexanecarboxylate (1.2 g, 81%) as a white powder.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-948fadc0160445599e6c171113a8f0c9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592454B2

Notizen zur Reaktion

Wird geladen…