Reacción #1483094

Ecuación de reacción

pTSA

DL-threonine

1-dodecanol

→

27

Rendimiento 101.5%

Dodecyl 2-amino-3-hydroxybutanoate

Rendimiento 101.5%

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-threonine 26 (5 g, 41.9 mmol) in toluene (100 mL) was added 1-dodecanol 2 (7 g, 37.7 mmol) in one lot, followed by pTSA (8.77 g, 46.16 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 27 (11 g, yield: 91%) as a liquid.

Fuente