Reaktion #1483096

Reaktionsgleichung

pTSA

DL-phenylalanine

dodecanol 2

→

39

Ausbeute 99.1%

Dodecyl 2-amino-3-phenylpropanoate

Ausbeute 99.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe temperature of the reaction mixture was slowly raised
2. 2
   Temperaturto reflux temperature
3. 3
   Sonstigethe water was separated azeotropically The reaction mixture
4. 4
   EinengenThe reaction mixture was concentrated under vacuum
5. 5
   Waschenwashed with aqueous 5% Na2CO3 (3×50 mL)
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Einengenconcentrated under vacuum

Vorschrift

To a stirred solution of DL-phenylalanine 38 (5 g, 30.26 mmol) in toluene (100 mL) was added dodecanol 2 (5.08 g, 27.24 mmol) in one lot, followed by pTSA (6.33 g, 33.29 mmol). 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 39 (9 g, yield: 89.1%) as a liquid.

Quelle