Reaction #51320

ord-14e183bf183e4aad9e636b0434eacf20

Reaction equation

Nc1ccc(Cl)cc1
4-chloroaniline
CC(=O)C(=O)OCC(C)C
iso-butyl pyruvate
→
CC(C)COC(=O)[C@H](C)Nc1ccc(Cl)cc1
title compound
CC(C)COC(=O)[C@H](C)Nc1ccc(Cl)cc1
N-(4-chlorophenyl)alanine iso-butyl ester

Reactants

Nc1ccc(Cl)cc1
4-chloroaniline
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=0.6 in 25% EtOAc/hexanes) and purification

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).

Source

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