3,4-Dichloroaniline → N-(3,4-dichlorophenyl)alanine 2-ethylbutyl Ester

HRID 1841114Notes

Reaction equation

HRID 1841114 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[C:10]([O:15][CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])(=[O:14])[C:11]([CH3:13])=O>>[CH2:20]([CH:17]([CH2:18][CH3:19])[CH2:16][O:15][C:10](=[O:14])[C@H:11]([CH3:13])[NH:5][C:4]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=1)[CH3:21]

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 2491952-Ethylbutyl pyruvate

Product 1

HCID 54258641N-(3,4-dichlorophenyl)alanine 2-ethylbutyl Ester

Procedure

Following General Procedure AA above and using 3,4-dichloroaniline (Aldrich) and 2-ethylbutyl pyruvate (prepared by following General Procedure AO above using 2-ethylbutanol (Aldrich) in place of iso-butanol), the title compound was prepared as an oil. The reaction was monitored by tlc on silica gel (Rf=0.6 in 25% EtOAc/hexanes) and purification was by preparative plate chromatography (silica gel using 25% EtOAc/hexanes as the eluant).

Workup

  1. customThe reaction was monitored by tlc on silica gel (Rf=0.6 in 25% EtOAc/hexanes) and purification

Sources & evidence

ORD record
ord-1e9abf7cdd064a9c8ce6137295a0ec55
Source dataset
uspto-grants-2004_01
Patent number
US06683075B1

Reaction notes

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