Triethylamine → Methyl 6-[[2-(2-ethyl-3,4-dimethoxyphenyl)ethyl]amino]-6-oxohexanoate

HRID 1493751Notes

Reaction equation

HRID 1493751 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](Cl)=[O:9].FC(F)(F)C([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=1[CH2:29][CH3:30])=O.C(N(CC)CC)C>ClCCl>[CH2:29]([C:20]1[C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=1[CH2:18][CH2:17][NH:16][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:11])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 520737Methyl 6-chloro-6-oxohexanoateHCID 143465332,2,2-Trifluoro-N-[2-(2-ethyl-3,4-dimethoxyphenyl)ethyl]acetamide

Product 1

HCID 14346544Methyl 6-[[2-(2-ethyl-3,4-dimethoxyphenyl)ethyl]amino]-6-oxohexanoateYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-chloro-6-oxohexanoic acid methyl ester (10 g) in dry dichloromethane (100 ml) was added dropwise to a stirred, cooled solution of Intermediate 2 (10.4 g) and triethylamine (5.65 g) in dry dichloromethane (100 ml). The reaction mixture was stirred for 1 h at room temperature, the solvent was removed in vacuo and the residue was purified by FCC using ether as eluent to give the title compound (15 g) as a white solid, m.p. 37°-39°.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-73576b2114b9493bb80773a000bf9398
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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