4-Chloroaniline → N-(4-chlorophenyl)alanine Iso-butyl Ester

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:13])[C:10]([CH3:12])=O>>[CH2:15]([O:14][C:9](=[O:13])[C@H:10]([CH3:12])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:16]([CH3:18])[CH3:17]

Participants

Reactant 2

HCID 78124-Chloroaniline

HCID 83084Isobutyl pyruvate

Product 1

HCID 54074575N-(4-chlorophenyl)alanine Iso-butyl Ester

Procedure

Following General Procedure AA above and using 4-chloroaniline (Aldrich) and iso-butyl pyruvate (prepared by following General Procedure AO above), 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

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

Sources & evidence

ORD record: ord-14e183bf183e4aad9e636b0434eacf20
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Reaction notes

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