2-Methoxyaniline → N-(2-methoxyphenyl)valine

HRID 1389375Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(OC1C=CC(N)=CC=1)C.Br[CH:21]([CH:39]([CH3:41])[CH3:40])[C:22]([O:24]CC1C=CC=C(OC2C=CC=CC=2)C=1)=[O:23]>>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C@H:21]([C:22]([OH:24])=[O:23])[CH:39]([CH3:41])[CH3:40]

Participants

Reactant 3

HCID 70002-Methoxyaniline

HCID 90764-Ethoxyaniline

HCID 13229492m-Phenoxybenzyl alpha-bromoisovalerate

Product 1

HCID 15383895N-(2-methoxyphenyl)valine

Procedure

Using the procedure of Example 1, each of 2-methoxyaniline and 4-ethoxyaniline is reacted with m-phenoxybenzyl α-bromoisovalerate to yield the m-phenoxybenzyl ester of N-(2-methoxyphenyl)valine, MS m/e 405.2 (M+), and the m-phenoxybenzyl ester of N-(4-ethoxyphenyl)valine, MS m/e 419.1 (M+).

Sources & evidence

ORD record: ord-f5d834b278ca442eaf67ac2c12819a6d
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243819

Reaction notes

Loading…