Hydroxyamine hydrochloride → diethyl 2-[4-[(1S,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]propanedioate

HRID 1617815Notes

Reaction equation

HRID 1617815 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH2:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=2)=O)=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].Cl.[NH2:37][OH:38].C(=O)([O-])O.[Na+]>>[CH2:1]([O:3][C:4](=[O:35])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH2:18]/[C:19](=[N:37]\[OH:38])/[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=2)=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666662372-{4-[(S)-3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-malonic acid diethyl ester

Product 1

HCID 136166863diethyl 2-[4-[(1S,3E)-3-hydroxyimino-1-(2-methylphenyl)-3-(2-methyl-4-pyridinyl)propyl]phenyl]propanedioate

Procedure

In analogy to example 1, step 2, from 2-{4-[(S)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-malonic acid diethyl ester and hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate was prepared the title compound as a mixture of E and Z isomers (2.7:1) as a white oil, MS (ESI+): m/z=489.3 ([M+H]+.

Sources & evidence

ORD record
ord-601ebce26f574c33a893410ba4eb8e45
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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