3-[5-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-[1,2,4]oxadiazol-3-ylmethyl]-benzoic acid → 4-[5-(4-Acetyl-2-chloro-3-hydroxy-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.[Cl:29][C:30]1[C:31]([OH:54])=[C:32]([C:51](=[O:53])[CH3:52])[CH:33]=[CH:34][C:35]=1[O:36][CH2:37][C:38]1[O:42][N:41]=[C:40]([CH2:43][C:44]2[CH:49]=[CH:48][C:47](I)=[CH:46][CH:45]=2)[N:39]=1>>[C:51]([C:32]1[CH:33]=[CH:34][C:35]([O:36][CH2:37][C:38]2[O:42][N:41]=[C:40]([CH2:43][C:44]3[CH:49]=[CH:48][C:47]([C:19]([OH:21])=[O:20])=[CH:46][CH:45]=3)[N:39]=2)=[C:30]([Cl:29])[C:31]=1[OH:54])(=[O:53])[CH3:52]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 of Example 140, employing 1-{3-chloro-2-hydroxy-4-[3-(4-iodo-benzyl)-[1,2,4]oxadiazol-5-ylmethoxy]-phenyl}-ethanone. 1H NMR (DMSO-d6) δ 13.05 (s, 1H), 12.86 (s, 1H), 7.92 (d, 1H), 7.85 (m, 2H), 7.38 (d, 2H), 6.84 (d, 1H), 5.72 (s, 2H), 4.18 (s, 2H), 2.59 (s, 3H). LC-MS (m/e): 401 (M−1).
Sources & evidence
- ORD record
- ord-6c9ea8d4be73497793051a4d834cec9b
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816523B2
Reaction notes
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