Potassium Iodide → Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate

HRID 1994305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994305
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([CH:12]([CH:18]([CH3:20])[CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2=[O:21])=[CH:4][CH:3]=1.Cl.Cl[CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CS(C)=O>[CH3:19][CH:18]([CH3:20])[CH:12]([N:9]1[CH2:10][CH2:11][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[C:8]1=[O:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 68541940Ethyl 2-(3-(4-hydroxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate

Produkt 1

HCID 68538692Ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 2-(3-(4-hydroxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (50 mg; 0.15 mmol) was dissolved in DMSO (1 ml). 4-Chloromethylpyridine hydrochloride (39 mg; 0.23 mmol), potassium carbonate (86 mg; 0.62 mmol) and potassium iodide (8 mg, 0.4 mmol) were successively added thereto. The mixture was heated at 50° C. for 3 h. Cooling to RT was followed by partitioning between water (10 ml) and EtOAc (10 ml). The phases were separated and the aqueous phase was extracted with EtOAc (3×; 5 ml). The combined organic phases were dried over MgSO4, and the solvent was removed under reduced pressure. Purification of the residue by column chromatography (SiO2) resulted in ethyl 3-methyl-2-{2-oxo-3-(4-(pyridin-4-ylmethoxy)benzyl)imidazolidin-1-yl}-butyrate (45 mg; 0.11 mmol). MS: 412.50 (M+H); Rt: 1.04 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Aufarbeitung

  1. temperatureCooling to RT
  2. customby partitioning between water (10 ml) and EtOAc (10 ml)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×; 5 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-876d6431d5cd460ca203aae8519928cc
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652143B2

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