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

HRID 1995681

Reaktionsgleichung

Reaktionsgleichung von HRID 1995681
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-b378435e412d489391329f93df72f6ad
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04405642

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