Reaction #71908

Reaction equation

N,N-diisopropylethylamine

serine methyl ester hydrochloride

3-methyl-4-nitrobenzoic acid

WSC hydrochloride

→

title compound

Yield 88.0%

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

Yield 88.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 1/0)

Procedure

The same operation as in Example (102a) was performed using serine methyl ester hydrochloride (5.24 g, 33.7 mmol), 3-methyl-4-nitrobenzoic acid (6.1 g, 33.7 mmol), WSC hydrochloride (6.71 g, 35 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (4.52 g, 35 mmol) and dichloromethane (100 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 1/0) to obtain 8.35 g of the title compound as a light yellow solid (88%).

Source