Hydrochloric Acid → 2-Methoxybenzyl 3-[[N-(3,4-Dimethoxyphenethyl)]amino]-2-hydroxypropionate

HRID 364253

反応式

HRID 364253 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:14])[C:11]([OH:13])=[O:12].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]O.Cl>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:14])[C:11]([O:13][CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[O:21][CH3:20])=[O:12]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 691542-Methoxybenzyl alcoholHCID 132310073-(3,4-Dimethoxyphenethyl)amino-2-hydroxypropionic acid

生成物 1

HCID 202406622-Methoxybenzyl 3-[[N-(3,4-Dimethoxyphenethyl)]amino]-2-hydroxypropionate収率 23%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To 3 g of the 3-(3,4-dimethoxyphenethyl)amino-2-hydroxypropionic acid prepared in Example I was added 200 ml of benzene and 20 ml of 2-methoxybenzyl alcohol. About 0.5 ml of concentrated HCl was added to catalyze the reaction. The reaction mixture was heated to reflux for 6 hours and the water was collected by a moisture trap. The reaction mixture was extracted with 200 ml of 0.5% HCl in water. The aqueous layer was basified with NaHCO3 and extracted with CHCl3. Evaporation of the CHCl3 gave an oily residue which after chromotography on a column (silica gel/Et2O:EtOH=5:1) gave 1 g (23%) of white solid: m.p. 79.5°-82.5° C. The NMR, IR and mass spectra were consistent with the assigned structure and the elemental analysis was consistent with the empirical formula C21H27O6N.

後処理

  1. customthe reaction
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 6 hours
  4. customthe water was collected by a moisture trap
  5. extractionThe reaction mixture was extracted with 200 ml of 0.5% HCl in water
  6. extractionextracted with CHCl3
  7. customEvaporation of the CHCl3
  8. customgave an oily residue which after chromotography on a column (silica gel/Et2O:EtOH=5:1)

出典と根拠

ORDレコード
ord-fd65adcc48ad47f8972f6d7244d7d433
出典データセット
uspto-grants-1986_08
特許番号
US04604481

関連ノート

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