4-Isobutylbenzoic acid → [4-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol
Reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.O[NH:38][C:39](=[NH:48])[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=1>CN(C=O)C>[CH3:13][CH:2]([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[O:10][N:48]=[C:39]([C:40]3[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=3)[N:38]=2)=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A solution of 10.0 g (56.2 mmol) of 4-(2-methylpropyl)benzoic acid, 10.8 g (56.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 7.6 g (56.2 mmol) of 1-hydroxybenzotriazole hydrate in 70 mL of DMF was stirred at rt for 30 min. N-Hydroxy-4-(hydroxymethyl)benzamidine (9.3 g, 56.2 mmol, from Step A) was added to the reaction mixture at rt and the resulting slurry was stirred at 140° C. for additional 2 h. The reaction was cooled to rt and quenched with 50 mL of water. The aqueous layer was extracted with 200 mL of ethyl acetate. The organic layer was washed with 0.5 N HCl solution, saturated NaHCO3 solution and water and then was concentrated to dryness to afford 16.5 g of the title compound: 1H NMR (400 Mhz, CD3OD) δ 0.95 (d, J=6.7, 6H), 1.96 (m, 1H), 2.61 (d, J=7.3, 2H), 7.42 (d, J=8.0, 2H), 7.54 (d, J=8.2, 2H), 8.13 (m, 4H).
Workup
- temperatureThe reaction was cooled to rt
- customquenched with 50 mL of water
- extractionThe aqueous layer was extracted with 200 mL of ethyl acetate
- washThe organic layer was washed with 0.5 N HCl solution, saturated NaHCO3 solution and water
- concentrationwas concentrated to dryness
Sources & evidence
- ORD record
- ord-20d6b7c51aa54f60ac71a686f5783224
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199142B2
Reaction notes
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