2'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid → N-methyl-N-(3-{5-[2'-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine
Reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH2:20])=[N:18][OH:19])[CH:12]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][C:32]([C:35](O)=O)=[CH:31][C:30]=1[C:38]([F:41])([F:40])[F:39]>>[CH3:9][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[N:20]=[C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH3:22])=[C:30]([C:38]([F:39])([F:41])[F:40])[CH:31]=3)[O:19][N:18]=2)[CH:12]=1)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21].[CH3:9][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[N:20]=[C:35]([C:32]3[CH:33]=[CH:34][C:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH3:22])=[C:30]([C:38]([F:39])([F:41])[F:40])[CH:31]=3)[O:19][N:18]=2)[CH:12]=1)[CH2:7][C:6]([OH:5])=[O:21]Participants
4
Reactant 2
Product 2
Procedure
Tert-butyl N-methyl-N-(3-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate was prepared following the general procedure 7 starting from Intermediate 21 and Intermediate 5. It was hydrolyzed following procedure 8, affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.55 (s, 1H), 8.50 (d, J=8.0 Hz, 1H), 8.36 (s, 1H), 8.23 (d, J=7.8 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.78-7.63 (m, 2H), 7.42-7.12 (m, 3H), 7.17 (d, J=7.4 Hz, 1H), 4.51 (s, 2H), 4.12 (s, 2H), 2.81 (s, 3H), 2.02 (s, 3H). HPLC (Method A); Rt 4.20 min (Purity: 99.48%). CHN analysis: [C26H22O3F3N3—HCl] Calculated: C, 60.29%, H, 4.48%, N, 8.11%. Found: C, 60.08%, H, 4.42%, N, 7.91%.
Sources & evidence
- ORD record
- ord-e60747e3dcc44b159f4343b24e38d13a
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802704B2
Reaction notes
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