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

HRID 988465

Reaction equation

HRID 988465 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][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:14])[C:11]([CH3:13])=O>>[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)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 11769098Benzyl 2-oxopropanoate

Product 1

HCID 15434839N-(3,4-dichlorophenyl)alanine Benzyl Ester

Procedure

Following General Procedure AA above and using 3,4-dichloroaniline (Aldrich) and benzyl pyruvate (prepared by following General Procedure AO above using benzyl alcohol in place of iso-butanol), the title compound was prepared as an oil. The reaction was monitored by tlc on silica gel (Rf=0.4 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=0.4 in 25% EtOAc/hexanes) and purification

Sources & evidence

ORD record
ord-017c1fb331ca4e659ba0d031955b0425
Source dataset
uspto-grants-2003_10
Patent number
US06635632B1

Linked notes

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