Sodium Hydroxide → 3-{3'-[3-(4-Butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoic acid

HRID 250887Notes

Reaction equation

HRID 250887 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:37])[N:16]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[CH:26][CH:25]=3)[CH:21]=[CH:22][CH:23]=2)[CH3:17])=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH3:6]>O1CCCC1.CO>[CH2:3]([O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:37])[N:16]([C:18]2[CH:19]=[C:20]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:29]=3)[CH:21]=[CH:22][CH:23]=2)[CH3:17])=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67273394Ethyl 3-{3'-[3-(4-butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoate

Product 1

HCID 115324163-{3'-[3-(4-Butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a manner similar to that of Example (19g), by reaction of 200 mg (5.0 mmol, 4.8 eq) of sodium hydroxide and 490 mg (1.03 mmol, 1 eq) of ethyl 3-{3′-[3-(4-butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoate in 6 ml of a tetrahydrofuran/methanol mixture (8/2), and after recrystallization from ethyl acetate/heptane, 330 mg of 3-{3′-[3-(4-butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoic acid are obtained in the form of white crystals. (m.p.=165° C.). Yield=71%

Workup

  1. customafter recrystallization from ethyl acetate/heptane, 330 mg of 3-{3′-[3-(4-butoxyphenyl)-1-methylureido]biphenyl-4-yl}propanoic acid
  2. customare obtained in the form of white crystals

Sources & evidence

ORD record
ord-6bc913f3e0ad4f0db42ec7650ec05391
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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