Reacción #1909790

Ecuación de reacción

3,5-dihydroxy-2-naphthoic acid

L-phenylalanine methyl ester hydrochloride

WSC.HCl

HOBT

N-methylmorpholine

→

title compound

Rendimiento 61.0%

(2S)-3-Phenyl-2-(3,5-dihydroxy-2-naphthoylamino)propionic acid methyl ester

Rendimiento 61.0%

Disolventes

Water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe organic layer was washed successively with a 10% aqueous citric acid solution, water
3. 3
   Secadoa saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate-1/1 v/v)

Procedimiento

A solution of 3,5-dihydroxy-2-naphthoic acid (4.08 g), L-phenylalanine methyl ester hydrochloride (4.74 g), WSC.HCl (4.22 g), HOBT (2.97 g) and N-methylmorpholine (2.41 ml) in DMF (200 ml) was stirred at room temperature for 16 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a 10% aqueous citric acid solution, water, a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate-1/1 v/v) to give the title compound (4.42 g, yield 61%).

Fuente