n-Heptyl isocyanate → Methyl 3-[3'-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate

HRID 250832

Reaktionsgleichung

[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1.O1CCCC1.C(N(CC)CC)C>O>[CH3:11][N:12]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

1.2 mL (7.43 mmol, 2 eq) of heptyl isocyanate are added to a solution of 1.0 g (3.7 mmol, 1 eq) of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (obtained as in 4c) in 15 mL of a 4/1 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 12 hours at 40° C. The reaction is stopped by addition of 10 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.15 g of methyl 3-[3′-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate are obtained. Yield=76%

Aufarbeitung

extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-800f07e77d51499d8878a360cbebb2cd
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07863332B2

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