تفاعل #1483085

ord-51f3d29847f74da5b8d778ed4ea542de

معادلة التفاعل

Cc1ccc(S(=O)(=O)O)cc1
pTSA
CC(N)C(=O)O
DL-alanine
CCCCCCCCCCC(C)O
dodecanol 2
CCCCCCCCCCCCOC(=O)C(C)N
dodecyl 2-aminopropanoate
المردود 110.8%
CCCCCCCCCCCCOC(=O)C(C)N
Dodecyl 2-aminopropanoate
المردود 110.8%

المتفاعلات

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONAfter addition
  2. 2
    درجة الحرارةthe temperature of the reaction mixture was slowly raised
  3. 3
    درجة الحرارةto reflux temperature
  4. 4
    أخرىthe water was separated azeotropically
  5. 5
    تركيزThe reaction mixture was concentrated under vacuum
  6. 6
    غسيلwashed with aqueous 5% Na2CO3 (3×50 mL)
  7. 7
    تجفيفThe organic layer was dried over Na2SO4
  8. 8
    تركيزconcentrated under vacuum

الإجراء التجريبي

To a stirred solution of DL-alanine 1 (5 g, 56.1 mmol) in toluene (100 mL) was added dodecanol 2 (9.42 g, 50.5 mmol) in one lot, followed by pTSA (11.75 g, 61.7 mmol). After 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 crude dodecyl 2-aminopropanoate 3 (14.4 g, yield: 100%) as a liquid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08900625B2uspto-grants-2014_12