DL-alanine → Dodecyl 2-aminopropanoate

HRID 1395903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1395903
[NH2:1][CH:2]([C:4]([OH:6])=[O:5])[CH3:3].[CH3:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17](O)[CH3:18].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]([CH3:3])[C:4]([O:6][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 602DL-alanineHCID 6101p-Toluenesulfonic acidHCID 25045Dodecan-2-ol

Produkt 1

HCID 6453806Dodecyl 2-aminopropanoateAusbeute 110,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionAfter addition
  2. temperaturethe temperature of the reaction mixture was slowly raised
  3. temperatureto reflux temperature
  4. customthe water was separated azeotropically
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. washwashed with aqueous 5% Na2CO3 (3×50 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-51f3d29847f74da5b8d778ed4ea542de
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08900625B2

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