Acetic Acid → HCID 178451523, Verbindung

HRID 1042427Notizen

Reaktionsgleichung

[C:1]([C:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]([CH3:16])([CH3:15])[C:4]=1O)#[N:2].O.[NH2:19][NH2:20].CC(O)=O>C(O)C>[NH2:2][C:1]1[NH:20][N:19]=[C:4]2[C:5]([CH3:16])([CH3:15])[N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][C:3]=12

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

32 g of tert-Butyl 4-cyano-3-hydroxy-2,2-dimethyl-2,5-dihydro-1H-pyrrole-1-carboxylate (0.134 mol) were added to 430 ml of absolute ethanol. To this solution, 9 ml (0.18 mol) of hydrazine hydrate were added, followed by 12 ml of glacial AcOH (1.5 eq); The mixture was stirred at 60° C. for 48 hours, the ethanol was removed, the residue was taken up with 400 ml of sodium hydrogencarbonate solution, and extracted several times with ethyl acetate up to total extraction of the desired product. The organic phases were dried and evaporated. After purification by flash chromatography (eluent: CHCl3/EtOH 97/3) and trituration with a mixture of hexane/ethyl acetate 9/1, 25 g of title compound were obtained. Total yield 30.5 g (yield: 88%)

Aufarbeitung

customthe ethanol was removed
extractionextracted several times with ethyl acetate
extractionup to total extraction of the desired product
customThe organic phases were dried
customevaporated
customAfter purification by flash chromatography (eluent: CHCl3/EtOH 97/3) and trituration
additionwith a mixture of hexane/ethyl acetate 9/1

Quellen und Nachweise

ORD-Eintrag: ord-3e250c84243442dcb9921608b5e6b3fe
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08557857B2

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