Methyl 4-(4-{[(3,5-Dimethylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate → 4-(4-{[(3,5-Dimethylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoic Acid
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])(=[O:11])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1>Cl>[CH3:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[O:16][C:17]=2[CH3:18])(=[O:11])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1Participants
3
Procedure
Method C. Reaction of benzoate 25 (346 mg, 0.87 mmol) and 6 M HCl (10 mL) gave acid 26 (335 mg, 100%) as a white solid: mp (H2O) 265-268° C.; 1H NMR δ 13.16 (br s, 1 H, CO2H), 8.05 (dd, J=8.5, 1.8Hz, 2 H, H-2, H-6), 7.93 (ddd, J=8.5, 1.8Hz, 2 H, H-3, H-5), 7.41 (br s, 2 H, H-2′, H-6′), 7.37 (br s, 1 H, H-4′), 4.62 (s, 2 H, CH2SO2), 2.32 (s, 6 H, 2×CH3), 2.19 (s, 3 H, CH3); MS m/z 386.5 (MH+, 100%). Anal. calcd for C20H19NO5S: C, 62.32; H, 4.97; N, 3.63. Found: C, 62.59; H, 4.84; N, 3.58%.
Sources & evidence
- ORD record
- ord-f5ba806daa0b4073af1bdf8508e397b3
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085570B2
Reaction notes
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