Sodium Hydroxide → 3-[2-Butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoic acid

HRID 250900Notes

Reaction equation

HRID 250900 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:35])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH:21]=1)[CH2:4][CH2:5][CH3:6]>O1CCCC1.CO>[CH2:3]([O:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:11]=[CH:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]([CH3:35])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH:21]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272912Methyl 3-[2-butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate

Product 1

HCID 115322653-[2-Butoxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoic acidYield 46%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 400 mg (10 mmol, 7.5 eq) of sodium hydroxide and methyl 3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate, obtained in the preceding step, in 6 ml of a tetrahydrofuran/methanol mixture (8/2), and after crystallization from pentane, 220 mg of 3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=78° C.). Yield=46% over the two steps.

Workup

  1. customafter crystallization from pentane, 220 mg of 3-[2-butoxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoic acid

Sources & evidence

ORD record
ord-d545ed31d23a43c595d5c912d1510359
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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