3-[5-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-[1,2,4]oxadiazol-3-ylmethyl]-benzoic acid → 4-[5-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-[1,2,4]oxadiazol-3-ylmethyl]-benzoic acid
Reaction equation
C(C1C=CC(OCC2ON=C(CC3C=C(C=CC=3)[C:19]([OH:21])=[O:20])N=2)=C(C)C=1O)(=O)C.[OH:29][C:30]1[C:35]([CH3:36])=[C:34]([O:37][CH2:38][C:39]2[O:43][N:42]=[C:41]([CH2:44][C:45]3[CH:50]=[CH:49][C:48](I)=[CH:47][CH:46]=3)[N:40]=2)[CH:33]=[CH:32][C:31]=1[C:52](=[O:54])[CH3:53]>>[C:52]([C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:38][C:39]2[O:43][N:42]=[C:41]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([C:19]([OH:21])=[O:20])=[CH:47][CH:46]=3)[N:40]=2)=[C:35]([CH3:36])[C:30]=1[OH:29])(=[O:54])[CH3:53]Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared essentially as described for 3-[5-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-[1,2,4]oxadiazol-3-ylmethyl]-benzoic acid, employing 1-{2-hydroxy-4-[3-(4-iodo-benzyl)-[1,2,4]oxadiazol-5-ylmethoxy]-3-methyl-phenyl}-ethanone. 1H NMR (DMSO-d6) δ 12.84 (s, 1H), 12.80 (s, 1H), 7.86 (m. 2H), 7.78 (d, 1H), 7.38 (d, 2H), 6.67 (d, 1H), 5.60 (s, 2H), 4.19 (s, 2H), 2.55 (s, 3H), 1.99 (s, 3H). LC-MS (m/e): 381 (M−1).
Sources & evidence
- ORD record
- ord-447f0d4b49674fdfad5a4e52f693799e
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816523B2
Reaction notes
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