2'-Chloro-2-(methoxymethyl)biphenyl-4-carboxylic acid → Tert-butyl N-(3-{5-[2'-chloro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][C:9]=1[CH2:17][O:18][CH3:19].[NH2:20][C:21](=[N:39][OH:40])[C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=1)[CH2:25][N:26]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:16][N:39]=[C:21]([C:22]3[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=3)[CH2:25][N:26]([CH3:27])[CH2:28][C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[N:20]=2)=[CH:10][C:9]=1[CH2:17][O:18][CH3:19].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:40][N:39]=[C:21]([C:22]3[CH:23]=[C:24]([CH:36]=[CH:37][CH:38]=3)[CH2:25][N:26]([CH3:27])[CH2:28][C:29]([OH:31])=[O:30])[N:20]=2)=[CH:10][C:9]=1[CH2:17][O:18][CH3:19]Participants
4
Reactant 2
Product 2
Procedure
Tert-butyl N-(3-{5-[2′-chloro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 4 starting from Intermediate 13 and Intermediate 21. It was hydrolyzed following the general procedure 8 affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.33 (s, 2H), 8.22 (m, 2H), 7.79-7.69 (m, 2H), 7.63 (m, 1H), 7.53-7.45 (m, 3H), 7.37 (m, 1H), 4.48 (s, 2H), 4.29 (d, J=13.1 Hz, 1H), 4.21 (d, J=13.1 Hz, 1H), 4.12 (s, 2H), 3.24 (s, 3H), 2.81 (s, 3H). LC/MS (Method B): 476.4 (M−H)−, 478.3 (M+H)+. HPLC (Method A) Rt 3.99 min (Purity: 98.4%).
Sources & evidence
- ORD record
- ord-e0edac63f5374564a1cf697edb602244
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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