Ethyl 3-(methylamino)propanoate → Methyl 3-[(2-ethoxycarbonyl-ethyl)-methyl-amino]-2-(4-ethyl-3,5-dimethoxyphenyl)-propionate

HRID 382805Notes

Reaction equation

HRID 382805 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11](=[CH2:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:5][C:4]=1[O:17][CH3:18])[CH3:2].[CH3:19][NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23]([CH2:22][CH2:21][N:20]([CH3:19])[CH2:16][CH:11]([C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([CH2:1][CH3:2])=[C:4]([O:17][CH3:18])[CH:5]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:24])[CH3:27]

Participants

3

Reactant 2

HCID 541480Ethyl 3-(methylamino)propanoateHCID 18361939Methyl 2-(4-ethyl-3,5-dimethoxy-phenyl)-acrylate

Product 1

HCID 18361927Methyl 3-[(2-ethoxycarbonyl-ethyl)-methyl-amino]-2-(4-ethyl-3,5-dimethoxyphenyl)-propionateYield 59.5%

Procedure

A solution of 78.4 g (313 mmol) of methyl 2-(4-ethyl-3,5-dimethoxy-phenyl)-acrylate and 47.7 g (364 mmol) of ethyl 3-methylamino-propionate was stirred at room temperature for 48 hours. Chromatography of the reaction mixture (silica gel, ethyl acetate/hexane 1:1) and crystallization from hexane gave 71.1 g (59%) of methyl 3-[(2-ethoxycarbonyl-ethyl)-methyl-amino]-2-(4-ethyl-3,5-dimethoxy-phenyl)-propionate as colorless crystals of m.p. 74-75°.

Workup

  1. customChromatography of the reaction mixture (silica gel, ethyl acetate/hexane 1:1) and crystallization from hexane

Sources & evidence

ORD record
ord-28aebf59640f4e84987340eb2be28b97
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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