Acetic Acid → b-(Z)-2-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylic acid
Reaction equation
[OH-].[Li+].C(O/[C:6](=[CH:12]\[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:34])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)/[C:7]([O:9]CC)=[O:8])C.[C:35](O)(=[O:37])[CH3:36].O>O1CCCC1.C(OCC)(=O)C>[CH3:36][CH2:35][O:37]/[C:12](/[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([CH3:34])[C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27])[N:20]=2)=[CH:15][CH:14]=1)=[CH:6]\[C:7]([OH:9])=[O:8]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 68 °C
Procedure
0.68 mL (0.68 mmol) of aqueous 1 M lithium hydroxide solution is added to a solution of 0.20 g (0.45 mmol) of ethyl (Z)-2-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}acrylate in 6 mL of tetrahydrofuran. The reaction mixture is stirred at 68° C. for 18 hours. After cooling, the reaction is worked up by addition of 0.68 mL (0.68 mmol) of aqueous 1 M acetic acid solution and 10 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. After filtration, the solvents are evaporated off.
Workup
- temperatureAfter cooling
- washwashed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration
- customthe solvents are evaporated off
Sources & evidence
- ORD record
- ord-1d5f4a48c45345fc858485df7fc3e5cd
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383652B2
Reaction notes
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