4-Isopropoxy-3-(methoxymethyl)benzoic acid → tert-butyl N-(2-fluoro-5-{5-[4-isopropoxy-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate
Reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH2:14][O:15][CH3:16])([CH3:3])[CH3:2].[NH2:17][C:18](=[N:37]O)[C:19]1[CH:20]=[CH:21][C:22]([F:36])=[C:23]([CH:35]=1)[CH2:24][N:25]([CH3:34])[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>>[F:36][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[N:17]=[C:9]([C:8]3[CH:12]=[CH:13][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:6]([CH2:14][O:15][CH3:16])[CH:7]=3)[O:11][N:37]=2)=[CH:35][C:23]=1[CH2:24][N:25]([CH3:34])[CH2:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28]Participants
3
Procedure
The title compound was prepared following procedure described for example 141, step 1, but starting from Intermediate 56 (134.55 mg; 0.60 mmol) and Intermediate 60 (177.47 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 8.24-8.20 (m, 2H), 8.11-8.04 (m, 2H), 7.17 (t, J=9.0 Hz, 1H), 6.98 (d, J=8.8 Hz, 1H), 4.70 (quint., J=6.1 Hz, 1H), 4.54 (s, 2H), 3.89 (s, 2H), 3.50 (s, 3H), 3.27 (s, 2H), 2.46 (s, 3H), 1.51 (s, 9H), 1.40 (d, J=6.0 Hz, 6H). LC/MS (Method B): 500.4 (M+H)+. HPLC (Method A) Rt 4.44 min (Purity: 97.6%).
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-38bd7031c1d3431d8211670f0a2ab203
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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