Water → 2-[4-(2-Carboxyethyl)phenyl]-4-(3-heptyl-1-methylureido)pyridinium acetate
Reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:33])[N:12]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:15]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O1CCCC1.CO.O>C(O)(=O)C>[C:28]([O-:30])(=[O:29])[CH3:27].[C:28]([CH2:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:16]2[CH:15]=[C:14]([N:12]([CH3:13])[C:11]([NH:10][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:33])[CH:19]=[CH:18][NH+:17]=2)=[CH:21][CH:22]=1)([OH:30])=[O:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (2.5 mmol, 4 eq) of sodium hydroxide are added to a solution of 260 mg (0.61 mmol, 1 eq) of ethyl 3-{4-[4-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate in 5 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for two hours at room temperature. The reaction is stopped by adding 20 mL of water and 3 mL of acetic acid and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then crystallized from pentane. 143 mg of 2-[4-(2-carboxyethyl)phenyl]-4-(3-heptyl-1-methylureido)pyridinium acetate are obtained. Yield=59%. m.p.=71-73° C.
Workup
- extractionis then extracted with ethyl acetate
- dry with materialdried over sodium sulfate
- customThe solvents are evaporated off
- customthe residue is then crystallized from pentane
Sources & evidence
- ORD record
- ord-b40b5040f7b44d558da1419d79351b6d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513297B2
Reaction notes
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