Hydrochloric Acid → 4-[1-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic Acid
Reaction equation
[CH2:1]([N:6]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([N:6]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:22])([CH3:23])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of methyl 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (190 mg) in 20 mL THF, 5 mL methanol 5 mL water was treated with lithium hydroxide hydrate (0.3 g) and stirred at room temperature for two hours. The mixture was diluted with 20 mL water, the pH adjusted to 2 with concentrated HCl and extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane), to yield 75 mg of 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (42) as a white solid. M.P.: 201-202° C.
Workup
- extractionextracted with three 25 mL portions of ethyl acetate
- dry with materialThe combined organic extracts were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a pale yellow solid
- customThe product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-6ac8b75ef90040c19f9c2db2f50483b3
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06838472B2
Reaction notes
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