反応 #1483094

反応方程式

pTSA

DL-threonine

1-dodecanol

→

27

収率 101.5%

Dodecyl 2-amino-3-hydroxybutanoate

収率 101.5%

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度the temperature of the reaction mixture was slowly raised
3. 3
   温度to reflux temperature
4. 4
   その他the water was separated azeotropically
5. 5
   濃縮The reaction mixture was concentrated under vacuum
6. 6
   洗浄washed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   乾燥The organic layer was dried over Na2SO4
8. 8
   濃縮concentrated under vacuum

実験手順

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.

出典