3,4-Dichloroaniline → N-(3,4-dichlorophenyl)alanine isopropyl ester

HRID 23028

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][CH:16]([CH3:18])[CH3:17])(=[O:14])[C:11]([CH3:13])=O>>[CH: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)([CH3:18])[CH3:17]

Participants

Reactant 2

HCID 72573,4-Dichloroaniline

HCID 9964097Isopropyl pyruvate

Product 1

HCID 54285545N-(3,4-dichlorophenyl)alanine isopropyl ester

Procedure

Following General Procedure AA above and using 3,4-dichloroaniline (Aldrich) and isopropyl pyruvate (prepared by following General Procedure AO above using isopropanol 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

customThe reaction was monitored by tlc on silica gel (Rf=0.4 in 25% EtOAc/hexanes) and purification

Sources & evidence

ORD record: ord-fdc87d00b5384ac88b4d61aa969f1d55
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Linked notes

Loading…