Hydrochloric Acid → 3-{4-[4-(2,4,6-Trimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804163

Reaktionsgleichung

[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=O)=[CH:9][CH:8]=2)[CH2:5][CH2:4][O:3]1.[OH-].[Na+].Cl.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(O)C>[CH3:29][C:24]1[CH:25]=[C:26]([CH3:28])[CH:27]=[C:22]([CH3:21])[C:23]=1[N:30]1[CH2:31][CH2:32][N:33]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])=[CH:17][CH:16]=2)=[O:13])[CH2:34][CH2:35]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To ethyl 4-(-2-oxooxazolidin-3-yl)benzoate (0.235 g) described in Preparation Example 12 were added 1 M aqueous sodium hydroxide solution (1.3 mL) and ethanol (5 mL), and the mixture was stirred at 50° C. 1N hydrochloric acid (1.3 mL) was added, 1-(2,4,6-trimethylphenyl)piperazine (0.215 g) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (0.277 g) were added, and the mixture was stirred at room temperature overnight. The mixture was extracted with ethyl acetate, washed with saturated brine, and the solvent was evaporated. The residue was purified by HPLC (ODS, 0.05% TFA aqueous solution-acetonitrile) to give the title compound (37.7 mg).

Aufarbeitung

stirringthe mixture was stirred at room temperature overnight
extractionThe mixture was extracted with ethyl acetate
washwashed with saturated brine
customthe solvent was evaporated
customThe residue was purified by HPLC (ODS, 0.05% TFA aqueous solution-acetonitrile)

Quellen und Nachweise

ORD-Eintrag: ord-540f18ada2da4cee81800e4aebeff0b0
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08354401B2

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