Reaction #1483105

Reaction equation

pTSA

DL-alanine

2-tridecanol

→

69

Yield 87.4%

Tridecan-2-yl 2-aminopropanoate

Yield 87.4%

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturethe temperature of the reaction mixture was slowly raised
3. 3
   Temperatureto reflux temperature
4. 4
   Otherthe water was separated azeotropically
5. 5
   ConcentrationThe reaction mixture was concentrated under vacuum
6. 6
   Washwashed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   DryingThe organic layer was dried over Na2SO4
8. 8
   Concentrationconcentrated under vacuum

Procedure

To a stirred solution of DL-alanine 1 (15 g, 168.5 mmol) in toluene (300 mL) was added 2-tridecanol 68 (30.3 g, 151.68 mmol) in one lot, followed by pTSA (35.26 g, 185.38 mmol). After the addition, the temperature of the reaction mixture was slowly raised to reflux temperature, the water was separated azeotropically and 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 69 (36 g, yield: 78.9%) as a liquid.

Source