Potassium Carbonate → HCID 178497309, Verbindung

HRID 541468Notizen

Reaktionsgleichung

Br[CH:2]1[CH2:6][CH:5]([O:7][CH3:8])[CH2:4][C:3]1=[O:9].Cl.[C:11]([C:14]1[C:15]([CH3:25])=[CH:16][C:17]([CH3:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20])(=[NH:13])[NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:9][C:3]12[CH2:4][CH:5]([O:7][CH3:8])[CH2:6][CH:2]1[NH:13][C:11]([C:14]1[C:15]([CH3:25])=[CH:16][C:17]([CH3:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20])=[N:12]2

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Into around-bottom flask, was placed a solution of 2-bromo-4-methoxycyclopentanone (compound 461.4, 600 mg, 1.86 mmol, 60%) in ACN (15 mL). Methyl 5-carbamimidoyl-2,4-dimethylbenzoate hydrochloride (compound 2.5, 320 mg) and potassium carbonate (430 mg, 3.11 mmol) were added and the mixture was stirred overnight at 80° C. The mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (50 mL) and then washed with brine (2×20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent to obtain the title compound as a brown oil (200 mg, 27%).

Aufarbeitung

customInto around-bottom flask, was placed
concentrationThe mixture was concentrated in vacuo
additionthe residue was diluted with ethyl acetate (50 mL)
washwashed with brine (2×20 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent

Quellen und Nachweise

ORD-Eintrag: ord-f5bd0cae0a5742eda753d980856a10da
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08871790B2

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