Sodium Hydroxide → (E)-3-[5'-(3-heptyl-1-methylureido)-2'-methylbiphenyl-4-yl]acrylic acid

HRID 250865Notes

Reaction equation

HRID 250865 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>O1CCCC1.CO>[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272904ethyl(E)-3-[5'-(3-heptyl-1-methylureido)-2'-methylbiphenyl-4-yl]acrylate

Product 1

HCID 11589595(E)-3-[5'-(3-heptyl-1-methylureido)-2'-methylbiphenyl-4-yl]acrylic acidYield 37%

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, 4.7 eq) of sodium hydroxide and 460 mg (1.05 mmol, 1 eq) of ethyl (E)-3-[5′-(3-heptyl-1-methylureido)-2′-methylbiphenyl-4-yl]acrylate in 6 ml of a tetrahydrofuran/methanol mixture (8/2), and after crystallization from a dichloromethane/pentane mixture, 160 mg of (E)-3-[5′-(3-heptyl-1-methylureido)-2′-methylbiphenyl-4-yl]acrylic acid are obtained in the form of a white powder. (m.p.=159° C.). Yield=37%

Workup

  1. customafter crystallization from a dichloromethane/pentane mixture, 160 mg of (E)-3-[5′-(3-heptyl-1-methylureido)-2′-methylbiphenyl-4-yl]acrylic acid
  2. customare obtained in the form of a white powder

Sources & evidence

ORD record
ord-1eb2081e33b64b04abd428bdd340735b
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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