Homoveratrylamine → 3-(3,4-Dimethoxyphenethyl)amino-2-hydroxypropionic acid

HRID 364252

반응식

HRID 364252 반응식
Cl[CH2:2][CH:3]([OH:7])[C:4]([OH:6])=[O:5].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:13][CH2:14][NH2:15].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH2:13][CH2:14][NH:15][CH2:2][CH:3]([OH:7])[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 3

HCID 8421HomoveratrylamineHCID 10340Sodium CarbonateHCID 92899Chlorolactic acid

생성물 1

HCID 132310073-(3,4-Dimethoxyphenethyl)amino-2-hydroxypropionic acid수율 61.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

A mixture of 20 g (0.16 mole) of β-chlorolactic acid and 86 g (0.48 mole) of 3,4-dimethoxyphenethylamine was heated at 110° C. for 15 hours. The resulting product was dissolved in about 200 ml of water and the pH was adjusted to about 8 with Na2CO3. The aqueous solution was extracted with 2×500 ml of chloroform and neutralized to pH 7 with diluted HCl. The solution was evaporated to dryness and the residue was recrystallized in EtOH to give 24.6 g (61.6%) of crystals: m.p. 187.5°-188.5° C. The NMR, IR and mass spectra were consistent with the assigned structure, and the elemental analysis was consistent with the empirical formula, C13H19O5N.

후처리

  1. extractionThe aqueous solution was extracted with 2×500 ml of chloroform and neutralized to pH 7 with diluted HCl
  2. customThe solution was evaporated to dryness
  3. customthe residue was recrystallized in EtOH

출처 및 근거

ORD 기록
ord-b677abee12214c0c8f90c99a7e15b55b
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604481

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