Methyl Isocyanate → 1-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionyl]-3-methyl-urea

HRID 1935285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1935285
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]=[C:26]=[O:27]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[C:8]([NH:10][C:26]([NH:25][CH3:24])=[O:27])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 12228Methyl IsocyanateHCID 224679093-Cyclopentyl-2-(4-phenoxy-phenyl)-propionamide

Produkt 1

HCID 99254051-[3-Cyclopentyl-2-(4-phenoxy-phenyl)-propionyl]-3-methyl-ureaAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 3-cyclopentyl-2-(4-phenoxy-phenyl)-propionamide (143 mg, 0.46 mmol) in toluene (10 mL) was treated with methyl isocyanate (0.04 mL, 0.69 mmol). The reaction mixture was heated under reflux for 24 h. The reaction was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionyl]-3-methyl-urea (116 mg, 69%) as a white solid: EI-HRMS m/e calcd for C22H26N2O3 (M+) 366.1943, found 366.1946.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe reaction was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-872391a968794e12a1a22f5cf397f2af
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384220B2

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