Hydroxyamine hydrochloride → 5-[(E)-C-[(2S)-2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1618042Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29].C(=O)([O-])O.[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[N:28]\[OH:29])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 666685065-[(S)-3-(4-Bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 580434645-[(E)-C-[(2S)-2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 151, step 3, 5-[(S)-3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1-methyl-1H-pyridin-2-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as a white foam, MS (ESI+): m/z=425.0 [M+H]+.

Sources & evidence

ORD record: ord-a0496e37c1864b10b6973627a493eda5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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