Reacción #1909791

ord-629b7224b37c4aacbd88982eeb240429

Ecuación de reacción

O=C(O)c1ccc(-c2ccc(O)cc2)cc1
4-(4-hydroxyphenyl)benzoic acid
CCOC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine ethyl ester hydrochloride
CCN=C=NCCCN(C)C.Cl
WSC.HCl
On1nnc2ccccc21
HOBT
CCOC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(-c2ccc(O)cc2)cc1
title compound
CCOC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(-c2ccc(O)cc2)cc1
4-(4-Hydroxyphenyl)benzoyl-L-phenylalanine ethyl ester

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

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 hydrogen-carbonate solution, water and saturated brine, dried over magnesium sodium sulfate
  4. 4
    Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE039088E1uspto-grants-2006_05