Allyl isocyanate → 1-allyl-3-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-urea

HRID 1860164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860164
[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]([N:22]=[C:23]=[O:24])[CH:20]=[CH2:21]>C1(C)C=CC=CC=1>[CH2:19]([NH:22][C:23]([NH:10][C:8](=[O:9])[C@@H:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:24])[CH:20]=[CH2:21]

Komponenten

4

Edukt 2

HCID 15123Allyl isocyanateHCID 462222313-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide

Produkt 1

HCID 120444671-allyl-3-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-ureaAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide (prepared in Example 13, 1.02 g, 3.55 mmol) in toluene (30 mL) was treated with allyl isocyanate (0.47 mL, 5.33 mmol). This solution was heated to reflux for 16 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 1-allyl-3-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-urea (1.06 g, 81%) as a colorless oil: [α]23589=25.2° (c=0.151, chloroform); EI-HRMS m/e calcd for C18H22Cl2N2O2 (M+) 368.1058, found 368.1054.

Aufarbeitung

  1. temperatureThis solution was heated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e0ca28096cd14e4f933289f02a19ccea
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528543B1

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