(4-Mercapto-5-methoxy-2-methyl-phenoxy)-acetic Acid Methyl Ester → {5-Methoxy-2-methyl-4-[5-(4-trifluoromethyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-phenoxy}-acetic acid
Reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[O:5][N:4]=1.C[O:19][C:20](=[O:33])[CH2:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([SH:31])=[CH:25][C:24]=1[CH3:32]>C(O)(=O)C>[CH3:30][O:29][C:27]1[C:26]([S:31][CH2:2][C:3]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[O:5][N:4]=2)=[CH:25][C:24]([CH3:32])=[C:23]([CH:28]=1)[O:22][CH2:21][C:20]([OH:33])=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Preparation of {5-Methoxy-2-methyl-4-[5-(4-trifluoromethyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-phenoxy}-acetic acid methyl ester (compound 43A) The title compound was prepared in a manner analogous to Example 1F using 42C and 1D. MS m/z 468 (M+1). Step 2. Preparation of {5-Methoxy-2-methyl-4-15-(4-trifluoromethyl-phenyl)-isoxazol-3-ylmethylsulfanyl]-phenoxy}-acetic acid (compound 43) The title compound was prepared in a manner analogous to Example 1 using 43A. IR cm−1: 1745, 1322; 400 MHz 1H NMR (DMSO-d6) δ 12.96 (br(s), 1H), 8.01 (d, 2H, J=8.3 Hz), 7.83 (d, 2H, J=8.3 Hz), 7.07 (s, 2H), 6.52 (s, 1H), 4.70 (s, 2H), 4.03 (s, 2H), 3.71 (s, 3H), 1.99 (s, 3H); MS m/z 454 (M+1). Anal. Calc'd for C21H18F3NO3S. 0.1H2O C, 54.46; H, 3.92; N, 3.01 found: C, 54.54; H, 3.74; N, 2.93.
Workup
- customwas prepared in a manner analogous to Example 1F
Sources & evidence
- ORD record
- ord-be41a9bf727a44dd8d30e37c47e37def
- Source dataset
- uspto-grants-2007_11
- Patent number
- USRE039916E1
Reaction notes
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