反応 #1909790

反応方程式

3,5-dihydroxy-2-naphthoic acid

L-phenylalanine methyl ester hydrochloride

WSC.HCl

HOBT

N-methylmorpholine

→

title compound

収率 61.0%

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

収率 61.0%

溶媒

Water

DMF

反応条件

後処理

1. 1
   抽出the mixture was extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed successively with a 10% aqueous citric acid solution, water
3. 3
   乾燥a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate-1/1 v/v)

実験手順

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%).

出典