Diisopropylethylamine → (S)-3-Methyl-2-[3-(2-methyl-quinolin-4-yl)-ureido]-butyric acid

HRID 2223716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223716
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13](NC2C3C(=CC=CC=3)N=C(C)C=2)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.C[O:29][C:30](=[O:36])[C@H:31]([CH:33]([CH3:35])[CH3:34])[NH2:32].CCN(C(C)C)C(C)C>CO>[CH3:34][CH:33]([CH3:35])[C@H:31]([NH:32][C:13]([NH:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1)=[O:14])[C:30]([OH:29])=[O:36]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 111190Methyl valinate hydrochlorideHCID 179565591,3-Bis-(2-methyl-quinolin-4-yl)urea

Produkt 1

HCID 59715919(S)-3-Methyl-2-[3-(2-methyl-quinolin-4-yl)-ureido]-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 1,3-bis-(2-methyl-quinolin-4-yl)-urea (342.4 mg, 1 mmol), valin methyl ester hydrochloride (167.6 mg, 1 mmol) and DIPEA (0.34 mL, 2 mmol) in MeOH (10 mL) is heated at 80° C. for 15 h. The solvent is evaporated and the residue is dissolved in 6N aqueous HCl (6 mL). The reaction mixture is heated at 90° C. for 12 h. Evaporation and purification by preparative HPLC provides the title compound.

Aufarbeitung

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in 6N aqueous HCl (6 mL)
  3. temperatureThe reaction mixture is heated at 90° C. for 12 h
  4. customEvaporation and purification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-193e665612ec4b8fbba5690dc79fd78b
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375227B2

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