Reaktion #993082

Reaktionsgleichung

EtOAc

4-hydroxy-7-(methoxycarbonyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

glycine benzyl ester hydrochloride

diisopropylethylamine

→

desired product

Ausbeute 27.5%

methyl 3-((2-(benzyloxy)-2-oxoethyl)carbamoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-7-carboxylate

Ausbeute 27.5%

Lösungsmittel

H2O

DCM

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted with DCM (3×)
3. 3
   Waschenthe organics were washed with H2O (2×)
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto yield a yellow solid

Vorschrift

4-hydroxy-7-(methoxycarbonyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (107 mg, 386 μmol), glycine benzyl ester hydrochloride (117 mg, 579 μmol), pybop (603 mg, 1158 μmol), and diisopropylethylamine (403 μl, 2316 μmol) were dissolved in DMF and stirred at room temperature for 24 hours. The reaction mixture was diluted with H2O and DCM, the layers were separated and the aqueous layer was extracted with DCM (3×), the organics were washed with H2O (2×) and dried over MgSO4, filtered and concentrated to yield a yellow solid. Flash column chromatography was performed using 2:1 Hex/EtOAc to give 45 mg of desired product.

Quelle