Reacción #1483096

Ecuación de reacción

pTSA

DL-phenylalanine

dodecanol 2

→

39

Rendimiento 99.1%

Dodecyl 2-amino-3-phenylpropanoate

Rendimiento 99.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe temperature of the reaction mixture was slowly raised
2. 2
   Temperaturato reflux temperature
3. 3
   Otrothe water was separated azeotropically The reaction mixture
4. 4
   ConcentraciónThe reaction mixture was concentrated under vacuum
5. 5
   Lavadowashed with aqueous 5% Na2CO3 (3×50 mL)
6. 6
   SecadoThe organic layer was dried over Na2SO4
7. 7
   Concentraciónconcentrated under vacuum

Procedimiento

To a stirred solution of DL-phenylalanine 38 (5 g, 30.26 mmol) in toluene (100 mL) was added dodecanol 2 (5.08 g, 27.24 mmol) in one lot, followed by pTSA (6.33 g, 33.29 mmol). The temperature of the reaction mixture was slowly raised to reflux temperature, and the water was separated azeotropically The reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The obtained residue was taken in ethyl acetate (200 mL) and washed with aqueous 5% Na2CO3 (3×50 mL) followed by brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 39 (9 g, yield: 89.1%) as a liquid.

Fuente