Reaction #71872

Reaction equation

serine methyl ester hydrochloride

3-methoxy-4-nitrobenzoic acid

WSC hydrochloride

N,N-diisopropylethylamine

→

title compound

Yield 69.0%

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

Yield 69.0%

Solvents

Dichloromethane

Conditions

Workup

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

Procedure

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%).

Source