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

HRID 364252

Reaktionsgleichung

Reaktionsgleichung von HRID 364252
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]

Komponenten

5

Edukt 3

HCID 8421HomoveratrylamineHCID 10340Sodium CarbonateHCID 92899Chlorolactic acid

Produkt 1

HCID 132310073-(3,4-Dimethoxyphenethyl)amino-2-hydroxypropionic acidAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b677abee12214c0c8f90c99a7e15b55b
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604481

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