تفاعل #1909790

معادلة التفاعل

3,5-dihydroxy-2-naphthoic acid

L-phenylalanine methyl ester hydrochloride

WSC.HCl

HOBT

N-methylmorpholine

→

title compound

المردود 61.0%

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

المردود 61.0%

المذيبات

Water

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر