n-Heptyl isocyanate → Methyl 3-[3'-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoate
Reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][O:12][C:13]1[CH:18]=[C:17]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:16]=[CH:15][C:14]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH3:32])[CH:26]=1.O1CCCC1.C(N(CC)CC)C>O>[CH2:1]([NH:8][C:9](=[O:10])[N:31]([C:27]1[CH:26]=[C:25]([C:14]2[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:13]=2[O:12][CH3:11])[CH:30]=[CH:29][CH:28]=1)[CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
540 μL (3.3 mmol, 2 eq) of heptyl isocyanate are added to a solution of 495 mg (1.65 mmol, 1 eq) of methyl 3-(2-methoxy-3′-methylaminobiphenyl-4-yl)propanoate in 10 mL of an 8/2 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 12 hours at room temperature. The reaction medium is hydrolyzed in water 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). 525 mg of methyl 3-[3′-(3-heptyl-1-methylureido)-2-methoxybiphenyl-4-yl]propanoate are obtained in oil form. Yield=72%
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)
Sources & evidence
- ORD record
- ord-cc0a2df2975d4b1cbb3a22253289dd34
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863332B2
Reaction notes
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