3-Phenylpropyl isocyanate → Ethyl 3-{3'-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate
Reaktionsgleichung
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][NH:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1>ClCCl.C(N(CC)CC)C>[CH3:13][N:14]([C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[C:11]([NH:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
188 μL (1.2 mmol, 1.5 eq) 3-phenylpropyl isocyanate are added to a solution of 230 mg (0.81 mmol, 1 eq) of ethyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (prepared in Example 7c) in 10 mL of an 8/2 dichloromethane/triethylamine mixture. The reaction medium is stirred at 40° C. for 12 hours and then hydrolyzed with water and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residual oil is chromatographed on silica (7/3 heptane/ethyl acetate). 348 mg of ethyl 3-{3′-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate are obtained in solid form. Yield=96%
Aufarbeitung
- extractionhydrolyzed with water and extracted with ethyl acetate
- washwashed with sodium chloride solution
- dry with materialdried over sodium sulfate
- customThe solvents are evaporated off
- customthe residual oil is chromatographed on silica (7/3 heptane/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-a1543b0243a846b2837b49971130c72e
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07863332B2
Notizen zur Reaktion
Wird geladen…