Water → (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylic acid

HRID 390652Notes

Reaction equation

HRID 390652 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[C:27](\[CH3:33])/[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O1CCCC1.CO.O>C(O)(=O)C>[CH2:3]([NH:10][C:11](=[O:34])[N:12]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[C:27](\[CH3:33])/[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 16225425ethyl (E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylateHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 16224224(E)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylic acidYield 44.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.5 g (2.5 mmol) of sodium hydroxide are added to a solution of 1.2 g (2.5 mmol) of ethyl (E)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylate in 30 mL of an 8/2 tetrahydrofuran/methanol mixture. The reaction medium is stirred at room temperature for 4 hours. After addition of water and acidification to pH4 with acetic acid, the reaction medium is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. The product is recrystallized from an isopropyl ether/pentane mixture. 456 mg (40%) of (E)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-methylacrylic acid are obtained in the form of a solid with a melting point of 79° C.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 7/3 heptane/ethyl acetate mixture
  9. customThe product is recrystallized from an isopropyl ether/pentane mixture

Sources & evidence

ORD record
ord-d92833a8d27540baa44b15e8d3aff59a
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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