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

HRID 364253

Reaction equation

HRID 364253 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fd65adcc48ad47f8972f6d7244d7d433
Source dataset
uspto-grants-1986_08
Patent number
US04604481

Linked notes

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