2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid → tert-butyl N-(5-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzyl)-N-methyl-beta-alaninate
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=O)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2].[NH2:21][C:22](=[N:42][OH:43])[C:23]1[CH:24]=[CH:25][C:26]([F:41])=[C:27]([CH:40]=1)[CH2:28][N:29]([CH3:39])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:43][N:42]=[C:22]([C:23]3[CH:24]=[CH:25][C:26]([F:41])=[C:27]([CH:40]=3)[CH2:28][N:29]([CH3:39])[CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared following procedure described for example 141, step 1, but starting from Intermediate 36 (162.20 mg; 0.60 mmol) and Intermediate 63 (185.47 mg; 0.57 mmol), the crude mixture was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1) to afford the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.42 (d, J=1.4 Hz, 1H), 8.23 (dd, J=7.1, 1.4 Hz, 1H), 8.17 (dd, J=7.9, 1.8 Hz, 1H), 8.12-8.08 (m, 1H), 7.41-7.10 (m, 6H), 4.27-4.17 (m, 2H), 3.66 (br s, 2H), 3.33 (s, 3H), 2.08 (t, J=7.0 Hz, 2H), 2.52-2.31 (m, 4H), 2.28 (s, 3H), 1.45 (s, 9H), 1.05 (t, J=7.5 Hz, 3H). LC/MS (Method B): 560.5 (M+H)+. HPLC (Method A) Rt 5.14 min (Purity: 94.0%).
Workup
- customThe title compound was prepared following procedure
- customthe crude mixture was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)
Sources & evidence
- ORD record
- ord-07a588b446cc448db8f696c345e16f4a
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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