3,4,5-Trimethoxyaniline → N-(3,4,5-trimethoxyphenyl)valine

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])[NH2:6].Br[CH:15]([CH:33]([CH3:35])[CH3:34])[C:16]([O:18]CC1C=CC=C(OC2C=CC=CC=2)C=1)=[O:17]>>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([NH:6][C@H:15]([C:16]([OH:18])=[O:17])[CH:33]([CH3:35])[CH3:34])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

Reactant 2

HCID 322853,4,5-Trimethoxyaniline

HCID 13229492m-Phenoxybenzyl alpha-bromoisovalerate

Product 1

HCID 54160440N-(3,4,5-trimethoxyphenyl)valine

Procedure

By the above procedure, 3,4,5-trimethoxyaniline is reacted with m-phenoxybenzyl α-bromoisovalerate to yield the m-phenoxybenzyl ester of N-(3,4,5-trimethoxyphenyl)valine. MS m/e 465.2 (M+, 39.0), 182.9 (100).

Sources & evidence

ORD record: ord-0fe78fea00624dfca574602063e6de16
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243819

Reaction notes

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