2'-Chloro-2-(methoxymethyl)biphenyl-4-carboxylic acid → Tert-butyl n-(4-{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:38]=[CH:37][C:25]([CH2:26][N:27]([CH3:36])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:24][CH:23]=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:16][N:39]=[C:21]([C:22]3[CH:38]=[CH:37][C:25]([CH2:26][N:27]([CH3:36])[CH2:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[CH:24][CH:23]=3)[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]=[CH:24][C:25]([CH2:26][N:27]([CH3:36])[CH2:28][C:29]([OH:31])=[O:30])=[CH:37][CH:38]=3)[N:20]=2)=[CH:10][C:9]=1[CH2:17][O:18][CH3:19]Participants
4
Reactant 2
Product 2
Procedure
Tert-butyl N-(4-{5-[2′-chloro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 3 starting from Intermediate 13 and Intermediate 31. It was deprotected following the general procedure 8 affording the title compound as a white powder. LC/MS (Method B): 476.2 (M−H)−, 478.1 (M+H)+. HPLC (Method A) Rt 3.95 min (Purity: 99.5%). Melting point: 194-200° C.
Sources & evidence
- ORD record
- ord-51c5604cae0949908d329b138e49421e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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