Reacción #1483095

Ecuación de reacción

pTSA

DL-valine

1-dodecanol

→

Dodecyl 2-amino-3-methylbutanoate

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
9. 9
   Otroto afford
10. 10
    Otrocrude 35 (40 g, yield, 82%) as a liquid

Procedimiento

To a stirred solution of DL-valine 34 (20 g, 170.7 mmol) in toluene (200 mL) was added 1-dodecanol 2 (28.6 g, 153 mmol) in one lot, followed by pTSA (35.7 g, 187.7 mmol). After addition, 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 35 (40 g, yield, 82%) as a liquid.

Fuente