Hydrochloric Acid → isopentyl 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoate

HRID 2249655

Reaktionsgleichung

Reaktionsgleichung von HRID 2249655
[CH3:1][CH:2]([CH3:38])[CH2:3][C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[N:16]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH:17]=[C:18]([C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:19]=2)=[O:14])=[CH:9][C:8]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=O.[OH-].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+].[CH2:48](I)[CH2:49][CH:50](C)C>O1CCCC1.CN(C)C=O.O.C(OCC)(=O)C.C(Cl)(Cl)Cl.C(O)C>[CH2:26]([N:16]1[CH:17]=[C:18]([C:20](=[O:25])[CH2:21][CH:22]([CH3:23])[CH3:24])[CH:19]=[C:15]1[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:4][CH2:3][CH:2]([CH3:1])[CH3:38])=[C:8]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH2:37][CH:49]([CH3:50])[CH3:48])=[O:34])[CH:9]=1)=[O:14])[CH2:27][CH:28]([CH3:29])[CH3:30]

Komponenten

12

Edukt 5

HCID 313Hydrochloric Acid2×HCID 109241-Iodo-3-methylbutaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178164722-(3-ethoxy-3-oxopropyl)-4-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate

Produkt 1

HCID 68985376isopentyl 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.68 g of 2-(3-ethoxy-3-oxopropyl)-4-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}phenyl 3-methylbutanoate in 4 ml of tetrahydrofuran is dropwise added to a mixture of 14 ml of ethanol and 13 ml of 1 mol/L sodium hydroxide solution at 40-50° C., and the mixture thus obtained is stirred at the same temperature as above for one hour. Water and chloroform are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is dissolved in 14 ml of N,N-dimethylformamide, 0.89 g of potassium carbonate and 0.9 ml of isopentyl iodide are added, and the mixture thus obtained is stirred at 100° C. for 15 minutes. The reaction mixture cooled to ambient temperature is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 0.69 g of isopentyl 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoate.

Aufarbeitung

  1. customthe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customthe mixture thus obtained
  8. stirringis stirred at 100° C. for 15 minutes
  9. customthe organic layer is separated
  10. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent is distilled off under reduced pressure
  13. customThe residue is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c73475212e8f4e12bb21c433a38e5a40
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314888B1

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