Water → 3-[3-Fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid
Reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]([O:14]C)=[O:13].O1CCCC1.CO.O>C(O)(=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (2.5 mmol, 8 eq) of sodium hydroxide are added to a solution of 130 mg (0.3 mmol, 1 eq) of methyl 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 3 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for 3 hours at room temperature. The reaction is stopped by addition of 10 mL of water and 1 mL of acetic acid and 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 chromatographed on silica gel (70/30 heptane/ethyl acetate). The oil obtained is crystallized from heptane/dichloromethane. 55 mg of 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid in the form of a white solid are obtained (m.p.=92-93° C.). Yield=43%
Workup
- extractionextracted with ethyl acetate
- dry with materialdried over sodium sulfate
- customThe solvents are evaporated off
- customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)
- customThe oil obtained
- customis crystallized from heptane/dichloromethane
Sources & evidence
- ORD record
- ord-03ceecdf6d364c7ea181381f6f635724
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863332B2
Reaction notes
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