Hydroxyamine hydrochloride → 2-fluoro-4-[4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]phenyl]benzoic acid

HRID 1617642Notes

Reaction equation

HRID 1617642 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=O)=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].Cl.[NH2:37][OH:38].C([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18]/[C:19](=[N:37]\[OH:38])/[C:21]3[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH3:28])[CH:22]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 670155383-Fluoro-4'-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid

Product 1

HCID 580432612-fluoro-4-[4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]phenyl]benzoic acid

Procedure

In analogy to example 151, step 3, 3-fluoro-4′-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid was reacted with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound containing less than 10% of the corresponding Z isomer as a colorless solid, MS (ESI+): m/z=485.3 [M+H]+.

Sources & evidence

ORD record
ord-6634db30ae3b4e188bd4a23cb56f0572
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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