Reaction #51305

ord-6888b8e4ce4c4a608f80013bbcb300d7

Reaction equation

Nc1ccc(Cl)c(Cl)c1
3,4-dichloroaniline
CC(=O)C(=O)OCC(C)C
iso-butyl pyruvate
→
CC(C)COC(=O)[C@H](C)Nc1ccc(Cl)c(Cl)c1
title compound
CC(C)COC(=O)[C@H](C)Nc1ccc(Cl)c(Cl)c1
N-(3,4-dichlorophenyl)alanine iso-butyl ester

Reactants

Nc1ccc(Cl)c(Cl)c1
3,4-dichloroaniline
CC(=O)C(=O)OCC(C)C
iso-butyl pyruvate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction was monitored by tlc on silica gel (Rf=0.55 in 25% EtOAc/hexanes) and purification

Procedure

Following General Procedure AA above and using 3,4-dichloroaniline (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=0.55 in 25% EtOAc/hexanes) and purification was by preparative plate chromatography (silica gel using 25% EtOAc/hexanes as the eluant).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06849650B2uspto-grants-2005_02