Reacción #1483085

Ecuación de reacción

pTSA

DL-alanine

dodecanol 2

→

dodecyl 2-aminopropanoate

Rendimiento 110.8%

Dodecyl 2-aminopropanoate

Rendimiento 110.8%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturathe temperature of the reaction mixture was slowly raised
3. 3
   Temperaturato reflux temperature
4. 4
   Otrothe water was separated azeotropically
5. 5
   ConcentraciónThe reaction mixture was concentrated under vacuum
6. 6
   Lavadowashed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   SecadoThe organic layer was dried over Na2SO4
8. 8
   Concentraciónconcentrated under vacuum

Procedimiento

To a stirred solution of DL-alanine 1 (5 g, 56.1 mmol) in toluene (100 mL) was added dodecanol 2 (9.42 g, 50.5 mmol) in one lot, followed by pTSA (11.75 g, 61.7 mmol). After addition, the temperature of the reaction mixture was slowly raised to reflux temperature, the water was separated azeotropically, and 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 dodecyl 2-aminopropanoate 3 (14.4 g, yield: 100%) as a liquid.

Fuente