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Sodium Hydroxide → 3-[3'-(3-Heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoic acid

HRID 250850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 250850
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:38])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][C:21]=2[O:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>CO>[CH2:3]([NH:10][C:11](=[O:38])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][C:21]=2[O:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67271485Methyl 3-[3'-(3-heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoate

Produkt 1

HCID 115331433-[3'-(3-Heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

281 mg (7.03 mmol, 10 eq) of sodium hydroxide are added to a solution of 400 mg (0.703 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoate in 10 ml of methanol. The reaction mixture is heated at 55° C. for 1 hour. The reaction medium is evaporated to dryness, taken up in water, acidified with 2N hydrochloric acid solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over magnesium sulfate. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (10 g FlashSmart column) eluted with 30/70 heptane/ethyl acetate. The product is crystallized from heptane and 284 mg of 3-[3′-(3-heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoic acid are obtained in the form of white crystals (m.p.=60-62° C.). Yield=84%

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. customThe solvent is evaporated off
  6. customthe oil obtained
  7. customis chromatographed on silica gel (10 g FlashSmart column)
  8. washeluted with 30/70 heptane/ethyl acetate
  9. customThe product is crystallized from heptane and 284 mg of 3-[3′-(3-heptyl-1-methylureido)-2-(3-methylbutoxy)biphenyl-4-yl]propanoic acid

Quellen und Nachweise

ORD-Eintrag
ord-9549783122c84723bf1dcba770ee9c62
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07863332B2

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