반응 #1483094

반응 방정식

pTSA

DL-threonine

1-dodecanol

→

27

수율 101.5%

Dodecyl 2-amino-3-hydroxybutanoate

수율 101.5%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도the temperature of the reaction mixture was slowly raised
3. 3
   온도to reflux temperature
4. 4
   기타the water was separated azeotropically
5. 5
   농축The reaction mixture was concentrated under vacuum
6. 6
   세척washed with aqueous 5% Na2CO3 (3×50 mL)
7. 7
   건조The organic layer was dried over Na2SO4
8. 8
   농축concentrated under vacuum

실험 절차

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.

출처