Réaction #1483095

Équation de réaction

pTSA

DL-valine

1-dodecanol

→

Dodecyl 2-amino-3-methylbutanoate

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter addition
2. 2
   Températurethe temperature of the reaction mixture was slowly raised
3. 3
   Températureto reflux temperature
4. 4
   Autrethe water was separated azeotropically
5. 5
   ConcentrationThe reaction mixture was concentrated under vacuum
6. 6
   Lavagewashed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   SéchageThe organic layer was dried over Na2SO4
8. 8
   Concentrationconcentrated under vacuum
9. 9
   Autreto afford
10. 10
    Autrecrude 35 (40 g, yield, 82%) as a liquid

Mode opératoire

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.

Source