Reaktion #71872

Reaktionsgleichung

serine methyl ester hydrochloride

3-methoxy-4-nitrobenzoic acid

WSC hydrochloride

N,N-diisopropylethylamine

→

title compound

Ausbeute 69.0%

N-(3-Methoxy-4-nitrobenzoyl)serine methyl ester

Ausbeute 69.0%

Lösungsmittel

Dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction solution was washed with water and brine
2. 2
   Trocknendried over anhydrous magnesium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0)

Vorschrift

Dichloromethane (80 mL) was added to serine methyl ester hydrochloride (2.64 g, 17 mmol), 3-methoxy-4-nitrobenzoic acid (3 g, 15.2 mmol), WSC hydrochloride (3.83 g, 20 mmol), DMAP (0.18 g, 1.5 mmol) and N,N-diisopropylethylamine (2.58 g, 20 mmol), and the mixture was stirred at room temperature for one day. The reaction solution was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0) to obtain 3.11 g of the title compound as a colorless solid (69%).

Quelle