Pentane, 1-isocyanato- → Methyl 3-[3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate

HRID 250830

Reaktionsgleichung

Reaktionsgleichung von HRID 250830
[CH2:1]([N:6]=[C:7]=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:9][NH:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.O1CCCC1.C(N(CC)CC)C>O>[CH3:9][N:10]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)[C:7]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:8]

Komponenten

5

Edukt 3

HCID 206036Pentane, 1-isocyanato-HCID 67273433Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoateHCID 68616177Triethylamine tetrahydrofuran

Produkt 1

HCID 67273062Methyl 3-[3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

236 μL (1.84 mmol, 2 eq) of pentyl isocyanate are added to a solution of 250 mg (0.92 mmol, 1 eq) of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (obtained as in 4c) in 5 mL of a 9/1 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 12 h at room temperature. 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). 245 mg of methyl 3-[3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained. Yield=70%

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2605fc5eb73a4faab54d27b1da1b981b
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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