Reaction #1909791

Reaction equation

4-(4-hydroxyphenyl)benzoic acid

L-phenylalanine ethyl ester hydrochloride

WSC.HCl

HOBT

→

title compound

4-(4-Hydroxyphenyl)benzoyl-L-phenylalanine ethyl ester

Solvents

DMF

triethylamine

Water

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe organic layer was washed successively with a 10 % aqueous citric acid solution, water
3. 3
   Dryinga saturated aqueous sodium hydrogen-carbonate solution, water and saturated brine, dried over magnesium sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure

Procedure

To a solution of 4-(4-hydroxyphenyl)benzoic acid (3.0 g) and L-phenylalanine ethyl ester hydrochloride (3.38 g) in DMF (30 ml) were added WSC.HCl (2.7 g), HOBT (1.89 g) and triethylamine (2 ml), and the mixture was stirred at room temperature for 14 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 hydrogen-carbonate solution, water and saturated brine, dried over magnesium sodium sulfate, and concentrated under reduced pressure to give a crude product of the title compound.

Source