반응 #1909790

반응 방정식

3,5-dihydroxy-2-naphthoic acid

L-phenylalanine methyl ester hydrochloride

WSC.HCl

HOBT

N-methylmorpholine

→

title compound

수율 61.0%

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

수율 61.0%

용매

Water

DMF

반응 조건

후처리

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

실험 절차

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%).

출처