Butyl iodide → Methyl 3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate

HRID 250899Notes

Reaction equation

HRID 250899 reaction equation
I[CH2:2][CH2:3][CH2:4][CH3:5].[OH:6][C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH:9][C:8]=1[C:19]1[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])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:2]([O:6][C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH:9][C:8]=1[C:19]1[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])[CH:20]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 67273049HCID 67273049, compound

Product 1

HCID 67272912Methyl 3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 500 μL (4.4 mmol, 3.3 eq) of 1-iodobutane and 530 mg (1.33 mmol, 1 eq) of methyl 3-[2-hydroxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate in 10 ml of methyl ethyl ketone in the presence of 500 mg (3.61 mmol, 2.7 eq) of potassium carbonate at 80° C. for 16 hours, methyl 3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate is obtained in oil form and is used in the following reaction without further purification.

Sources & evidence

ORD record
ord-8ddca86af0d04103a8b4e2bf7f31f51e
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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