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

HRID 1995681

反応式

HRID 1995681 の反応式
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]

参加物

5

反応物 3

HCID 8421HomoveratrylamineHCID 10340Sodium CarbonateHCID 92899Chlorolactic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b378435e412d489391329f93df72f6ad
出典データセット
uspto-grants-1983_09
特許番号
US04405642

関連ノート

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