Acetic Acid → (Z)-3-[3'-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylic acid

HRID 390684Notes

Reaction equation

HRID 390684 reaction equation
[OH-].[Li+].[CH2:3]([NH:7][C:8](=[O:33])[N:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](\[O:30][CH2:31][CH3:32])/[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:10])[CH2:4][CH2:5][CH3:6].C(O)(=O)C>O1CCCC1>[CH2:3]([NH:7][C:8](=[O:33])[N:9]([C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[CH:19][C:20](/[CH:23]=[C:24](\[O:30][CH2:31][CH3:32])/[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:10])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 86626117ethyl (Z)-3-[3'-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate

Product 1

HCID 16225212(Z)-3-[3'-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylic acidYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.9 mL (2.9 mmol) of aqueous 1 M lithium hydroxide solution are added to a solution of 0.8 g (1.9 mmol) of ethyl (Z)-3-[3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate in 10 mL of tetrahydrofuran. The reaction medium is heated at reflux for 20 hours. After cooling, 3 mL (2.9 mmol) of 1 N acetic acid are added and the reaction medium is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, filtered and evaporated. 760 mg (100%) of (Z)-3-[3′-(3-butyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylic acid are obtained in the form of a white solid with a melting point of 126° C.

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionthe reaction medium is extracted with ethyl acetate
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-54103e5ac7c64455abe9fba714e24646
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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