4-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid → 3-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid
Reaction equation
C(C1C=CC(OCC2N=C(CC3C=CC(C(O)=O)=CC=3)ON=2)=C(Cl)C=1O)(=O)C.C([O:31][C:32](=[O:58])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][C:40]2[O:44][N:43]=[C:42]([CH2:45][O:46][C:47]3[CH:52]=[CH:51][C:50]([C:53](=[O:55])[CH3:54])=[C:49]([OH:56])[C:48]=3[Cl:57])[N:41]=2)[CH:34]=1)C>>[C:53]([C:50]1[CH:51]=[CH:52][C:47]([O:46][CH2:45][C:42]2[N:41]=[C:40]([CH2:39][C:35]3[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=3)[C:32]([OH:58])=[O:31])[O:44][N:43]=2)=[C:48]([Cl:57])[C:49]=1[OH:56])(=[O:55])[CH3:54]Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared essentially as described for 4-[3-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid, employing 3-[3-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[ 1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester. 1H NMR (DMSO-d6) δ 13.06 (s, 1H), 12.99 (s, 1H), 7.91 (m, 2H), 7.83 (m, 1H), 7.58 (m, 1H), 7.46 (dd, 1H), 6.89 (d, 1H), 5.49 (s, 2H), 4.48 (s, 2H), 2.59 (s, 3H). LC-MS (m/e): 401 (M−1).
Sources & evidence
- ORD record
- ord-66a1deff86fc45d6b70a72b77d3b0faf
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816523B2
Reaction notes
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