Isobutyl pyruvate → N-(4-azidophenyl)alanine Iso-butyl Ester

HRID 23048

Reaction equation

[N:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:11]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])(=[O:15])[C:12]([CH3:14])=O>>[CH2:17]([O:16][C:11](=[O:15])[C@H:12]([CH3:14])[NH:8][C:7]1[CH:9]=[CH:10][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=1)[CH:18]([CH3:20])[CH3:19]

Participants

Reactant 2

HCID 83084Isobutyl pyruvate

HCID 846744-Azidoaniline

Product 1

HCID 54176542N-(4-azidophenyl)alanine Iso-butyl Ester

Procedure

Following General Procedure AA above and using 4-azidoaniline (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=0.3 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=0.3 in 25% EtOAc/hexanes) and purification

Sources & evidence

ORD record: ord-8971890c899441279261f72e668f6918
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Linked notes

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