تفاعل #1483096

ord-409e2acf49cc4982802955bb3c65c021

معادلة التفاعل

Cc1ccc(S(=O)(=O)O)cc1
pTSA
NC(Cc1ccccc1)C(=O)O
DL-phenylalanine
CCCCCCCCCCC(C)O
dodecanol 2
CCCCCCCCCCCCOC(=O)C(N)Cc1ccccc1
39
المردود 99.1%
CCCCCCCCCCCCOC(=O)C(N)Cc1ccccc1
Dodecyl 2-amino-3-phenylpropanoate
المردود 99.1%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

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