Hydroxyamine hydrochloride → 4-Fluoro-4'-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-3-carboxylic acid
Reaction equation
COC(C1C=C(C2C=CC(C(C3C=CC=CC=3C)CC(C3C=CN=C(C)C=3)=O)=CC=2)C=CC=1F)=O.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][C:46]([CH:49]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=3[CH3:66])[CH2:50][C:51]([C:53]3[CH:58]=[CH:57][N:56]=[C:55]([CH3:59])[CH:54]=3)=O)=[CH:45][CH:44]=2)=[CH:39][C:38]=1[C:67]([OH:69])=[O:68].Cl.[NH2:71][OH:72].C([O-])(O)=O.[Na+]>>[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:44]=[CH:45][C:46]([CH:49]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=3[CH3:66])[CH2:50][C:51](=[N:71][OH:72])[C:53]3[CH:58]=[CH:57][N:56]=[C:55]([CH3:59])[CH:54]=3)=[CH:47][CH:48]=2)=[CH:39][C:38]=1[C:67]([OH:69])=[O:68]Participants
5
Reactant 4
Product 1
Procedure
In analogy to example 75, from 4-fluoro-4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-3-carboxylic acid methyl ester was prepared 4-fluoro-4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-3-carboxylic acid, which was directly subjected to the next step. In analogy to example 74, step 7, from 4-fluoro-4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-3-carboxylic acid and hydroxylamine hydrochloride in the presence of NaHCO3 was prepared the title compound as a mixture of E and Z isomers (3:1) as a colorless oil, MS (ESI+): m/z=469.1910 ([M+H]+).
Sources & evidence
- ORD record
- ord-eaad06fc5bc345f6ada7e4fa82e21846
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765730B2
Reaction notes
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