3,4,5-Trimethoxyaniline → 2,3,4-Trimethoxycyclohexylamine

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])N.C(C1C=C(C=C(C(O)=O)C=1)[NH2:20])(O)=O>>[CH3:1][O:2][CH:3]1[CH:9]([O:10][CH3:11])[CH:8]([O:12][CH3:13])[CH2:7][CH2:5][CH:4]1[NH2:20]

Participants

Reactant 2

HCID 322853,4,5-Trimethoxyaniline

HCID 668335-Aminoisophthalic acid

Product 1

HCID 225599332,3,4-Trimethoxycyclohexylamine

Procedure

3,4,5-trimethoxyaniline was hydrogenated via the procedure given for 3,5-dicarboxy-aniline to provide 2,3,4-trimethoxycyclohexylamine which was coupled to the C-terminal valine in the standard way.

Sources & evidence

ORD record: ord-a3a9e9d927f14451a6335b8df3b58b56
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864240B1

Reaction notes

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