Dl-Phenylalanine → Dodecyl 2-amino-3-phenylpropanoate

HRID 1395914노트

반응식

HRID 1395914 반응식
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23](O)[CH3:24].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][CH:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([O:12][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:11]

참가 물질

5

반응물 3

HCID 994Dl-PhenylalanineHCID 6101p-Toluenesulfonic acidHCID 25045Dodecan-2-ol

생성물 1

HCID 22005815Dodecyl 2-amino-3-phenylpropanoate수율 99.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-409e2acf49cc4982802955bb3c65c021
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08900625B2

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