Hydroxyamine hydrochloride → HCID 87237149, compound

HRID 1617849Notes

Reaction equation

[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:34])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22](=[O:25])[N:21]([CH3:26])[CH:20]=2)=O)=[CH:11][CH:10]=1)[CH:4]([CH3:6])[CH3:5].Cl.[NH2:36][OH:37].C(=O)([O-])O.[Na+]>>[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:34])[C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[CH2:16]/[C:17](=[N:36]\[OH:37])/[C:19]2[CH:24]=[CH:23][C:22](=[O:25])[N:21]([CH3:26])[CH:20]=2)=[CH:13][CH:14]=1)[CH:4]([CH3:5])[CH3:6]

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 67015662HCID 67015662, compound

Product 1

HCID 87237149HCID 87237149, compound

Procedure

In analogy to example 151, step 3, N—((S)-1-hydroxy-3-methylbutan-2-yl)-4-(3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxo-1-o-tolylpropyl)benzamide was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as an off-white solid containing <10% of the corresponding Z isomer, MS (ESI+): m/z=476.2 [M+H]+.

Sources & evidence

ORD record: ord-33aba106d998473eae534802c388f02f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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