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Sodium Hydroxide → 2-[1-[2-Butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyric acid

HRID 390666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 390666
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH2:21][CH3:22])/[C:16]([O:18]CC)=[O:17])[CH:11]=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:38])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:31])[CH:24]=1)[CH2:4][CH2:5][CH3:6]>C(O)C.O1CCCC1>[CH2:3]([O:7][C:8]1[CH:13]=[C:12](/[CH:14]=[C:15](\[CH2:21][CH3:22])/[C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:38])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:31])[CH:24]=1)[CH2:4][CH2:5][CH3:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68964170Ethyl 2-[1-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyrate

Produkt 1

HCID 162250092-[1-[2-Butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(e)-ylidene]butyric acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

40 mg (1 mmol) of sodium hydroxide are added to a solution of 483 mg (1 mmol) of ethyl 2-[1-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(E)-ylidene]butyrate in 1 mL of ethanol and 10 mL of tetrahydrofuran. The reaction mixture is heated at 50° C. for 48 hours. The reaction medium is evaporated to dryness, taken up in water and acidified with aqueous 2 N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. After filtration, the solvent is evaporated off and the oil obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture and then precipitated from heptane. 310 mg (83%) of 2-[1-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]meth-(E)-ylidene]butyric acid are obtained in the form of a white powder with a melting point of 98-100° C.

Aufarbeitung

  1. customThe reaction medium is evaporated to dryness
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated off
  7. customthe oil obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 60/40 heptane/ethyl acetate mixture
  10. customprecipitated from heptane

Quellen und Nachweise

ORD-Eintrag
ord-d66dab7b7b874a098af6e348cc665f74
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383652B2

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