DL-alanine → Dodecyl 2-aminopropanoate

HRID 1395903노트

반응식

HRID 1395903 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 6453806Dodecyl 2-aminopropanoate수율 110.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51f3d29847f74da5b8d778ed4ea542de
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08900625B2

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