2-Naphthylamine → N-(2-naphthyl)alanine isobutyl ester

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:12]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])(=[O:16])[C:13]([CH3:15])=O>>[CH2:18]([O:17][C:12](=[O:16])[C@H:13]([CH3:15])[NH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1)[CH:19]([CH3:21])[CH3:20]

Participants

Reactant 2

HCID 70572-Naphthylamine

HCID 83084Isobutyl pyruvate

Product 1

HCID 54457376N-(2-naphthyl)alanine isobutyl ester

Procedure

Following General Procedure AA above and using 2-aminonaphthalene (Aldrich) and iso-butyl pyruvate (prepared by following General Procedure AO above), the title compound was prepared as an oil. Purification was by preparative plate chromatography (silica gel using 25% EtOAc/hexanes as the eluant).

Workup

customPurification

Sources & evidence

ORD record: ord-2074f13ed9154ebd816f5085613c9c96
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849650B2

Reaction notes

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