Réaction #1483094

Équation de réaction

pTSA

DL-threonine

1-dodecanol

→

27

Rendement 101.5%

Dodecyl 2-amino-3-hydroxybutanoate

Rendement 101.5%

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

Mode opératoire

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.

Source