Hydrochloric Acid → 4-{5-Methyl-4-[(phenylsulfonyl)methyl]-1,3-oxazol-2-yl}benzoic Acid
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19].Cl>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20]Participants
3
Procedure
Method C. Reaction of benzoate 16 (290 mg, 0.78 mmol) and 6 M HCl (5 mL) gave acid 17 (278 mg, 100%) as a white solid: mp (H2O) 284-287° C.; 1H NMR δ 12.68 (br s, 1 H, CO2H), 8.04 (br d, J=8.4Hz, 2 H, H-2, H-6), 7.90 (br d, J=8.4 Hz, 2 H, H-3, H-5), 7.80 (br ddd, J=8.1, 1.9, 1.2Hz, 2 H, H-2′, H-6′), 7.75 (tt, J =7.5, 1.2Hz, 1 H, H-4′), 7.62 (br dd, J=8.1, 7.4Hz, 2 H, H-3′, H-5′), 4.68 (s, 2 H, CH2SO2), 2.13 (s, 3 H, CH3); MS m/z 358.8 (MH+, 100%).
Sources & evidence
- ORD record
- ord-5af34248141246eea4d72a4c931954cc
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085570B2
Reaction notes
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