Methanol → 1-{3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionyl}-3-methyl-urea

HRID 1935282

Reaktionsgleichung

Reaktionsgleichung von HRID 1935282
CO[C:3](=[O:26])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:27][NH:28][C:29]([NH2:31])=[O:30].C[O-].[Mg+2].C[O-].CO>>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)=[CH:13][CH:12]=2)[C:3]([NH:31][C:29]([NH:28][CH3:27])=[O:30])=[O:26])[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 674852183-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester

Produkt 1

HCID 224679331-{3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionyl}-3-methyl-ureaAusbeute 29 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester (245 mg, 0.71 mmol) and methyl urea (131 mg, 1.76 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 5.5 mL, 2.12 mmol). The reaction mixture was then concentrated in vacuo to approximately one-half the volume of methanol. The resulting reaction mixture was then heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then partitioned between water (20 mL) and ethyl acetate (50 mL). The layers were separated, and the aqueous layer was further extracted with ethyl acetate (1×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 1-{3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionyl}-3-methyl-urea (79 mg, 29%) as a white foam: mp 91-95° C. (foam to gel); FAB-HRMS m/e calcd for C24H27N3O2 (M+H)+ 390.2181, found 390.2192.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo to approximately one-half the volume of methanol
  2. customThe resulting reaction mixture
  3. temperaturewas then heated
  4. temperatureunder reflux for 15 h
  5. custompartitioned between water (20 mL) and ethyl acetate (50 mL)
  6. customThe layers were separated
  7. extractionthe aqueous layer was further extracted with ethyl acetate (1×25 mL)
  8. dry with materialThe combined organic extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-854b00ec8ce24542a2a39b552cc5be67
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384220B2

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